Water → Benzoic acid, 4-(acetylamino)-2-hydroxy-3-(2-propenyl)-, methyl ester

HRID 1084943Notes

Reaction equation

HRID 1084943 reaction equation
C([O:4][C:5]1[CH:14]=[C:13]([NH:15][C:16]([CH3:18])=[O:17])[CH:12]=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8])C=C.O.CN1C[CH2:24][CH2:23][C:22]1=O>>[OH:4][C:5]1[C:14]([CH2:24][CH:23]=[CH2:22])=[C:13]([NH:15][C:16]([CH3:18])=[O:17])[CH:12]=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8]

Participants

4

Reactant 3

HCID 962WaterHCID 13387N-methyl-2-pyrrolidone2×HCID 10586690HCID 10586690, compound2×

Product 1

HCID 10800613Benzoic acid, 4-(acetylamino)-2-hydroxy-3-(2-propenyl)-, methyl ester

Procedure

84 g of methyl 2-allyloxy-4-acetaminobenzoate and 84 g of N-methylpyrrolidone were introduced into a 500 ml round-bottomed flask. The contents were heated quickly to reflux which was then maintained for 30 minutes, and the solution was then cooled slightly and poured into water. Crystallation was immediate. The same operations were repeated with the same quantities of methyl 2-allyloxy-4-acetaminobenzoate and N-methylpyrrolidone and the products from the two trials were combined and cooled, drained, washed with water and dried at 50° C.

Workup

  1. temperatureThe contents were heated quickly
  2. temperatureto reflux which
  3. temperaturewas then maintained for 30 minutes
  4. temperaturethe solution was then cooled slightly
  5. temperaturecooled
  6. washwashed with water
  7. customdried at 50° C.

Sources & evidence

ORD record
ord-e8b5768364bb496f8a1b6f690452ecad
Source dataset
uspto-grants-1991_04
Patent number
US05006570

Reaction notes

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