Benzoic acid, 3-amino-5-ethoxy-, methyl ester (9CI)

In the compound prepared in Step 2 (6.1 kg, 27.1 mol), methanol (54 L) and purified water (54 L) were added, and 10percent-palladium/carbon (6.1 kg, 10percent wt/wt) was added thereto, followed by stirring under hydrogen gas conditions at 4 atm for 2.5 hours at room temperature. A mixture of 3-benzyloxycarbonylamino-5-ethoxy-benzoic acid methyl ester (D47) (15 g, 45.5 mmol, 1 equiv), 10percent palladium on charcoal (50percent wet, 1.5 g, 5percent w/w) and NH4COOH (15 g, 455 mmol, 10 equiv) H20 (50 ml) and MEOH (200 ml) was stirred at 50 C for 2h. The mixture was cooled to room temperature and the catalyst was filtered off through a pad of celite. Most of the MEOH was removed in vacuo and the residue was partitioned between saturated aqueous NAHC03 solution and AcOEt. The aqueous phase was re-extracted with AcOEt. The combined organic phases were dried over MGS04 and concentrated in vacuo to give 3-amino- 5-ethoxy-benzoic acid methyl ester (D49) (8.8 g, 99percent) as a pale green solid which was used in the next step without further purification. [M+H] + = 196.1, RT = 2.49 min

Molecular Weight:195.21
XLogP3:1.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:4
Exact Mass:195.08954328
Monoisotopic Mass:195.08954328
Topological Polar Surface Area:61.6
Heavy Atom Count:14
Complexity:196
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes