Aniline → Ethyl 2-methyl-3-oxo-3-(phenylamino)propanoate

HRID 1431284Notes

Reaction equation

HRID 1431284 reaction equation
[CH3:1][CH:2]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:3]([O:5]CC)=O.[NH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>N1C=CC=CC=1>[CH3:1][CH:2]([C:3](=[O:5])[NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

4

Reactant 2

HCID 6115AnilineHCID 11857Diethyl methylmalonate

Product 1

HCID 67509027Ethyl 2-methyl-3-oxo-3-(phenylamino)propanoate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Prepared according to Procedure A using diethyl 2-methylmalonate (24.485 g, 141 mmol), aniline (9.00 mL, 99 mmol) and pyridine (16 mL) to afford product as a colorless oil after purification by chromatography on silica gel, eluting with EtOAc gradient in hexane. 1H NMR (400 MHz, chloroform-d) δ ppm 8.66 (1H, br. s.), 7.55 (2H, d, J=7.8 Hz), 7.33 (2H, t, J=8.0 Hz), 7.13 (1H, t, J=7.4 Hz), 4.20-4.33 (2H, m), 3.46 (1H, q, J=7.2 Hz), 1.56 (3H, d, J=7.4 Hz), 1.26-1.39 (3H, m).

Workup

  1. customPrepared
  2. customto afford product as a colorless oil
  3. customafter purification by chromatography on silica gel
  4. washeluting with EtOAc gradient in hexane

Sources & evidence

ORD record
ord-2f1b8ac8e20f4b2f98911098da199bdb
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

Loading…