4-Hydroxybenzamide → HCID 136021432, compound

HRID 1445783Notes

Reaction equation

HRID 1445783 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][CH:3]=1.Cl[CH2:12][C:13](=O)[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16]>CO>[CH2:18]([O:17][C:15](=[O:16])[CH2:14][C:13]1[N:8]=[C:6]([C:5]2[CH:9]=[CH:10][C:2]([OH:1])=[CH:3][CH:4]=2)[O:7][CH:12]=1)[CH3:19]

Participants

4

Reactant 2

HCID 650524-HydroxybenzamideHCID 69484Ethyl 4-chloroacetoacetate2×

Product 1

HCID 136021432HCID 136021432, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 4-hydroxybenzamide (25.2 g, 0.18 mol) and ethyl chloroacetoacetate (90 mL) is heated to 110° C. After 1 h, more ethyl chloroacetoacetate (30 mL) is added, and continue to heat for 3 h more. The mixture is cooled to approximately 60° C., and MeOH is added. The mixture is filtered and dried to yield the title compound (36.6 g, 80%) as an off-white solid. MS (m/e): 248.3 (M+1)

Workup

  1. temperatureto heat for 3 h more
  2. temperatureThe mixture is cooled to approximately 60° C.
  3. filtrationThe mixture is filtered
  4. customdried

Sources & evidence

ORD record
ord-1706ad27c4e4494ba8c702792ac48dba
Source dataset
uspto-grants-2010_02
Patent number
US07666871B2

Reaction notes

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