Water → 3-Acetyloxy-5-oxo-5-phenylamino-2-pentenoic acid

HRID 703441Notes

Reaction equation

HRID 703441 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:8]([O:11][C:12]1[CH2:13][C:14](=[O:19])[O:15][C:16](=[O:18])[CH:17]=1)(=[O:10])[CH3:9].O>C(O)(=O)C>[C:8]([O:11][C:12]([CH2:13][C:14](=[O:19])[NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[CH:17][C:16]([OH:18])=[O:15])(=[O:10])[CH3:9]

Participants

5

Reactant 3

HCID 962WaterHCID 6115AnilineHCID 124390722,6-dioxo-3,6-dihydro-2H-pyran-4-yl acetate

Product 1

HCID 541950343-Acetyloxy-5-oxo-5-phenylamino-2-pentenoic acidYield 81%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

65.7 g (0.705 mol) of aniline are added to a stirred suspension of 120 g (0.705 mol) of 4-acetyloxy-2H,3H-pyran-2,6-dione in 250 ml of acetic acid. The reaction medium is stirred for 1 h at room temperature and is then diluted by adding 500 ml of water. The solid is drained, washed with water and dried in an oven (50° C.) for 24 h. 150 g (81%) of the expected compound, melting point 125°-126° C., are obtained.

Workup

  1. additionis then diluted
  2. washwashed with water
  3. customdried in an oven (50° C.) for 24 h

Sources & evidence

ORD record
ord-6a7a572d187e4b16af4fd22f580c4425
Source dataset
uspto-grants-1991_01
Patent number
US04983607

Reaction notes

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