Water → (2-Cyano-5-nitro-phenylamino)-acetic acid methyl ester

HRID 1041806Notes

Reaction equation

HRID 1041806 reaction equation
F[C:2]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[CH3:13][O:14][C:15](=[O:18])[CH2:16][NH2:17].C(N(CC)CC)C.O>CS(C)=O>[CH3:13][O:14][C:15](=[O:18])[CH2:16][NH:17][C:2]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 69221Glycine methyl esterHCID 27590482-Fluoro-4-nitrobenzonitrile

Product 1

HCID 67264411(2-Cyano-5-nitro-phenylamino)-acetic acid methyl esterYield 98%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 2-fluoro-4-nitro-benzonitrile (16.6 g, 0.1 mol), glycine methyl ester (16 g, 0.125 mol, 1.25 eq.) and triethylamine (20 g, 0.2 mol) in DMSO (250 mL) was stirred at 70° C. for 12 hours. Water (2 L) was added and the solid precipitate was collected by filtration. Washed with ether and dried to give (2-cyano-5-nitro-phenylamino)-acetic acid methyl ester (23 g, 97.8 mmol, 98%): 1H NMR (300 MHz, CDCl3) δ 7.61 (dd, 2H), 7.40 (d, 1H), 4.10 (d, 2H), 3.87 (s, 3H).

Workup

  1. filtrationthe solid precipitate was collected by filtration
  2. washWashed with ether
  3. customdried

Sources & evidence

ORD record
ord-1a8bda41f39347009c704cac94ef85ba
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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