Acetyl chloride → [Acetyl-(2-cyano-5-nitro-phenyl)-amino]-acetic acid methyl ester

HRID 1688149Notes

Reaction equation

HRID 1688149 reaction equation
[CH3:1][O:2][C:3](=[O:17])[CH2:4][NH:5][C:6]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:7]=1[C:15]#[N:16].[C:18](Cl)(=[O:20])[CH3:19]>CN(C1C=CN=CC=1)C>[CH3:1][O:2][C:3](=[O:17])[CH2:4][N:5]([C:18](=[O:20])[CH3:19])[C:6]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:7]=1[C:15]#[N:16]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 67264411(2-Cyano-5-nitro-phenylamino)-acetic acid methyl ester

Product 1

HCID 67263766[Acetyl-(2-cyano-5-nitro-phenyl)-amino]-acetic acid methyl esterYield 86%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

At 50° C., (2-cyano-5-nitro-phenylamino)-acetic acid methyl ester (0.5 g, 2.1 mmol) was heated in acetyl chloride (100 mL) for 3 hours in the presence of catalytic DMAP. The mixture was poured over ice and then partitioned between ethyl acetate (100 ml) and water (50 ml). The organic layer was washed once with 1 M NaOH (100 mL) and dried over sodium sulfate. Concentration and silica gel purification (EtOAc/hexanes 9:1) gave [acetyl-(2-cyano-5-nitro-phenyl)-amino]-acetic acid methyl ester (0.5 g, 1.8 mmol, 86%): 1H NMR (300 MHz, CDCl3) δ 8.59 (d, 1H), 8.36 (dd, 1H), 7.99 (d, 1H), 3.9 (b, 2H), 3.78 (s, 3H), 2.00 (s, 3H).

Workup

  1. additionThe mixture was poured over ice
  2. custompartitioned between ethyl acetate (100 ml) and water (50 ml)
  3. washThe organic layer was washed once with 1 M NaOH (100 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationConcentration and silica gel purification (EtOAc/hexanes 9:1)

Sources & evidence

ORD record
ord-9132cf1ed7fd40a2ae419ddf4da7299f
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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