HCID 11391466, compound → HCID 11413680, compound

HRID 1991188Notes

Reaction equation

HRID 1991188 reaction equation
[CH:1]([N:3]([C:10]1[C:15]([N+:16]([O-])=O)=[CH:14][CH:13]=[CH:12][C:11]=1[CH3:19])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])=[O:2]>CO>[NH2:16][C:15]1[CH:14]=[CH:13][CH:12]=[C:11]([CH3:19])[C:10]=1[N:3]([CH:1]=[O:2])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

3

Reactant 1

HCID 11391466HCID 11391466, compound

Product 1

HCID 11413680HCID 11413680, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of ethyl N-formyl-N-(2-methyl-6-nitrophenyl)glycinate (154 mg, 0.58 mmol) in methanol containing 5% Pd/C (35 mg) was hydrogenated at 1 atmosphere for 1 h. The mixture was filtered through a pad of celite, and the solvent was removed in vacuo affording ethyl N-(2-amino-6-methylphenyl)-N-formylglycinate, 127 mg (93%) as an oil. MS (ESI) m/z 237 [M+H]. 1H NMR (400 MHz, CDCl3) δ ppm 1.30 (t, J=7.2Hz, 3H), 2.14 (s, 3H), 3.60 (d, J=17 Hz, 1H), 4.32-4.18 (m, 2H), 4.70 (br. s, 2 H), 4.77 (d, J=17 Hz, 1H), 6.60 (app t, J=8.0 Hz, 2H), 7.05 (t, J=7.8 Hz, 1H), 8.11 (s,

Workup

  1. filtrationThe mixture was filtered through a pad of celite
  2. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-c5652210b4904b769a0473b2154a472b
Source dataset
uspto-grants-2010_01
Patent number
US07645784B2

Reaction notes

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