4-Methyl-3-nitrobenzonitrile

white to light yellow crystal powder

A. To a stirred solution of 4-methylbenzonitrile (lOg, 85.47mmol) in cone. H3-nitro-4-[(2-N, N-dimethylamino)ethenyl]benzonitrile (66). N, N-Dimethylformamide dimethyl acetal (12.1 g, 101 mmol) was added to a solution of nitrotoluene 63 (16.3 g, 101 mmol) in dry DMF (60 mL). The mixture was refluxed overnight under N2. The reaction mixture was poured into ice water to give a red solid (21.5 g, 99%): mp 122-126 C; 1H NMR delta 8.22 (d, J = 1.6 Hz, 1H), 7.84 (d, J = 13.2 Hz, 1H), 7.82 (d, J = 8.8 Hz, 1H), 7.65 (dd, J = 8.8 and 1.6 Hz, 1 H), 5.67 (d, J = 13.2 Hz, 1 H), 2.98 (s, 6H). Anal. (C11H11N3O2) C, H, N.; Reagents and conditions: (a) H2, 10% Pd/C, EtOH; (b) NaNO2, aq. H2SO4; (c) CH3l, NaH, DMF; (d) NBS, benzoyl peroxide, CCl4; (e) AgNO3, aq. EtOH; (f) DMFDMA, DMF; (g) NalO4; aq. THF; (h) diethyl phosphite, (i-Pr)2NEt, THF; (j) 2-nitropropane, NaOEt, EtOH; (k) NaNO2, aq. HCl, then CuCN, KCN; (I) MeOH, H2SO4; (m) DCC, DMAP, MeOH, CH2Cl2; (n) Red-Al, t-BuOK, pyrrolidine, MTBE; (o) NH2OH HCl, H2O/EtOH or Py/EtOH (p) NCS, DMF.; The synthesis of benzaldehyde chlorooxime synthons 52 is depicted in Scheme 4, below. Of the eight aldehydes 44e-f and 74a-f, only 44e and 74d were commercially available. The preparation of aldehyde 44f began with the known three-step transformation of EXAMPLE 158 3-(2-Methylaminomethyl-cyclopropyl)-1H-indole-6-carbonitrile A mixture of

Molecular Weight:162.15
XLogP3:2.1
Hydrogen Bond Acceptor Count:3
Exact Mass:162.042927438
Monoisotopic Mass:162.042927438
Topological Polar Surface Area:69.6
Heavy Atom Count:12
Complexity:225
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes