Pyridine → HCID 16044401, compound

HRID 268498Notes

Reaction equation

HRID 268498 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].N1C=CC=CC=1.[CH2:15]([C:17]1[CH:25]=[CH:24][C:20]([C:21](Cl)=[O:22])=[CH:19][CH:18]=1)[CH3:16]>C1C=CC=CC=1>[CH2:15]([C:17]1[CH:25]=[CH:24][C:20]([C:21]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[OH:8])=[O:22])=[CH:19][CH:18]=1)[CH3:16]

Participants

5

Reactant 3

HCID 1049PyridineHCID 58012-AminophenolHCID 853684-Ethylbenzoyl chloride

Product 1

HCID 16044401HCID 16044401, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 8.2 gm. of o-aminophenol in 70 cc. of dry pyridine is added a solution of p-ethylbenzoyl chloride (prepared from 10 gm. of p-ethylbenzoic acid and thionyl chloride) in 20 cc. of benzene. An exothermic reaction occurs and the reaction mixture is stirred overnight at ambient temperature. The mixture is concentrated in vacuo and taken up between a 1:1 mixture of benzene and ether and 2.5 N hydrochloric acid. The organic layer is washed with saturated sodium bicarboxate, water, then dried and concentrated. Recrystallization from benzene-hexane gives 4- ethyl-2'-hydroxybenzanilide, m.p. 103°-105°C.

Workup

  1. customAn exothermic reaction
  2. concentrationThe mixture is concentrated in vacuo
  3. additiontaken up between a 1:1 mixture of benzene and ether and 2.5 N hydrochloric acid
  4. washThe organic layer is washed with saturated sodium bicarboxate, water
  5. customdried
  6. concentrationconcentrated
  7. customRecrystallization from benzene-hexane

Sources & evidence

ORD record
ord-2caf4d10c1d849cb97602c585f99e733
Source dataset
uspto-grants-1976_03
Patent number
US03947582

Reaction notes

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