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Home > Encyclopedia > 5-Amino-1,3-dihydro-1-methyl-2H-indol-2-one

5-Amino-1,3-dihydro-1-methyl-2H-indol-2-one

5-Amino-1,3-dihydro-1-methyl-2H-indol-2-one structure

5-Amino-1,3-dihydro-1-methyl-2H-indol-2-one 

structure
  • CAS No:

    20870-91-1

  • Formula:

    C9H10N2O

  • Chemical Name:

    5-Amino-1,3-dihydro-1-methyl-2H-indol-2-one

  • Synonyms:

    2H-Indol-2-one,5-amino-1,3-dihydro-1-methyl-;2-Indolinone,5-amino-1-methyl-;5-Amino-1,3-dihydro-1-methyl-2H-indol-2-one;5-Amino-1-methyl-1,3-dihydroindol-2-one;5-Amino-1-methylindolin-2-one

  • Categories:

    Chemical Reagents  >  Organic Reagents

5-Amino-1,3-dihydro-1-methyl-2H-indol-2-one Basic Attributes

162.1885

162.19

DTXSID30627603

2933790090

Characteristics

46.3

0.3

1.3±0.1 g/cm3

109 °C

472℃

239℃

1.644

4.47E-09mmHg at 25°C

Safety Information

20/21/22-36/37/38

22-26-36/37/39

Harmful

P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P403+P233, P405, P501

H302

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 2 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

5-Amino-1,3-dihydro-1-methyl-2H-indol-2-one Use and Manufacturing

5-Amino-1-methylindolin-2-one; To a suspension of l-methyl-5-nitroindolin-2-one (92 mg, 0.48 mmol) in 20 mL MeOH, was Pd(C) (9.2 mg, 10 weight %) added. The round bottom flask was capped with a rubber septum and put under a hydrogen atmosphere. After 18 h the hydrogen gas was evacuated by introducing argon to the round bottom flask. The reaction mixture was filtered through celite. The celite was washed with EtOAc (2X 30 ml). The volatiles were evaporated to afford the title compound in quantitative yield.Step 3: Preparation of Step 3; Preparation of Step 4; Preparation of (R)-[2-hydroxy-3-(1-methyl-2-oxo-2, 3-dihydro-1H-indol-5-ylamino)-propyl]-carbamic acid tert-butyl ester; 5-Amino-1-methyl-1, 3-dihydro-indol-2-one (1.20 g, 7.40 mmol), (S)-oxiranylmethyl-carbamic acid tert-butyl ester (1.28 g, 7.40 mmol) and lithium trifluoromethanesulfonate (1.14 g, 7.398 mmol) in acetonitrile (10 ml) are heated at 70 C. for 1 hour. The reaction mixture is diluted with ethyl acetate, washed with water and brine, dried (Na2SO4) and evaporated. The residue is purified by flash column chromatography (70% EtOAc/Hexane) to give the title compound as a light brown solid. HPLC r.t. 3.20 min; MS for C17H25N3O4 m/z 336.4(M+H)+.Step 4: Preparation of (5R)-2-hydroxy-3-(1-methyl-2-oxo-2, 3-dihydro-1H-indol-5-ylamino)-propionic acid methyl ester 5-Amino-1-methyl-1, 3-dihydro-indol-2-one (Step 3, 1.40 g, 8.63 mmol), methyl (2R)-glycidate (0.882 g, 8.63 mmol), and lithium trifluoromethanesulfonate (1.33 g, 8.63 mmol) in acetonitrile (15 ml) are heated at 70 C. for 4 hours. The reaction mixture is diluted with ethyl acetate, washed with water and brine, dried (Na2SO4) and evaporated. The residue is purified by flash chromatography (70% EtOAc/Hexane) to give the title compound as a light brown solid. HPLC r.t. 2.44 min; MS for C13H16N2O4 m/z 265.0(M+H)+.

Computed Properties

Molecular Weight:162.19
XLogP3:0.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:162.079312947
Monoisotopic Mass:162.079312947
Topological Polar Surface Area:46.3
Heavy Atom Count:12
Complexity:205
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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