Aniline → Methyl 4-anilino-4-oxobutanoate

HRID 1373084

Reaction equation

HRID 1373084 reaction equation
Cl[CH2:2][C:3](=O)[CH2:4][C:5]([O:7][CH3:8])=[O:6].ClC(=O)CC(OC)=[O:14].[NH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(N)(=O)CCC(N)=O>>[CH3:8][O:7][C:5](=[O:6])[CH2:4][CH2:3][C:2]([NH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:14]

Participants

5

Reactant 4

HCID 6115AnilineHCID 8036SuccinamideHCID 36240Methyl 4-chloroacetoacetateHCID 123460Methyl malonyl chloride

Product 1

HCID 224712Methyl 4-anilino-4-oxobutanoate

Procedure

Using the same reaction conditions as described in Example 20-step a except that methyl 4-chloro-3-oxobutyrate replaced methyl 3-chloro-3-oxopropionate, aniline (2.33 g, 25 mmol) was converted to the succinamide compound (5.18 g, 100%) after purification by chromatography over silica gel. 1H NMR (400 MHz, CDCl3) δ: 7.70 (s, 1H), 7.50 (d, 2H), 7.30 (t, 2H), 7.09 (m, 1H), 3.70 (s, 3H), 2.73–2.65 (m, 4H).

Workup

  1. customthe same reaction conditions
  2. customafter purification by chromatography over silica gel

Sources & evidence

ORD record
ord-4177852deba4418f910d698c6c4a5d57
Source dataset
uspto-grants-2007_01
Patent number
US07160902B2

Linked notes

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