Ammonia → 5-Hydroxy-6-isoquinolinecarboxamide

HRID 236129Notes

Reaction equation

HRID 236129 reaction equation
C[O:2][C:3]([C:5]1[C:6]([OH:15])=[C:7]2[C:12](=[CH:13][CH:14]=1)[CH:11]=[N:10][CH:9]=[CH:8]2)=O.[NH3:16]>>[OH:15][C:6]1[C:5]([C:3]([NH2:16])=[O:2])=[CH:14][CH:13]=[C:12]2[C:7]=1[CH:8]=[CH:9][N:10]=[CH:11]2

Participants

3

Reactant 2

HCID 222Ammonia2×HCID 54242020Methyl 5-hydroxyisoquinoline-6-carboxylate

Product 1

HCID 185359865-Hydroxy-6-isoquinolinecarboxamide

Procedure

5-Hydroxy-6-isoquinolinecarboxylic acid methyl ester as reported by Dyke, S. F. et al., in Tetrahedron 1973, 29(6), 857-62, is reacted with excess ammonia in a steel bomb for 12-18 hr. The excess ammonia is allowed to evaporate and the residue is crystallized from a suitable solvent mix such as ethyl acetate-toluene to give the title compound.

Workup

  1. customto evaporate
  2. customthe residue is crystallized from a suitable solvent
  3. additionmix such as ethyl acetate-toluene

Sources & evidence

ORD record
ord-61a2fd3f58e4425ebe797f207e3a3f06
Source dataset
uspto-grants-1987_02
Patent number
US04642343

Reaction notes

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