Gamma-Aminobutyric Acid → HCID 71735139, compound

HRID 1480934Notes

Reaction equation

HRID 1480934 reaction equation
CO[C:3]([C:5]1[N:6]=[CH:7][C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][CH:11]=[C:10]([O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH:9]=2)=[O:4].[NH2:23][CH2:24][CH2:25][CH2:26][C:27]([OH:29])=[O:28].CO.Cl>C[O-].[Na+].O>[OH:15][C:14]1[C:13]2[C:8](=[CH:9][C:10]([O:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)=[CH:11][CH:12]=2)[CH:7]=[N:6][C:5]=1[C:3]([NH:23][CH2:24][CH2:25][CH2:26][C:27]([OH:29])=[O:28])=[O:4]

Participants

7

Reactant 4

HCID 119Gamma-Aminobutyric AcidHCID 313Hydrochloric AcidHCID 887MethanolHCID 86709142Methyl 4-hydroxy-7-phenoxyisoquinoline-3-carboxylate

Product 1

HCID 71735139HCID 71735139, compoundYield 94.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 10942334Sodium MethoxideSolvent

Procedure

A mixture of 4-hydroxy-7-phenoxy-isoquinoline-3-carboxylic acid methyl ester (100 mg, 0.34 mmol) and 4-aminobutyric acid (525 mg, 5.1 mmol) in 0.5 N NaOMe in MeOH solution (6.8 mL, 3.4 mmol) was heated to reflux overnight. Reaction mixture was diluted with water (100 mL) and acidified by 1 N HCl solution to pH=3-4. Precipitate was collected and rinsed with water. It was dried in vacuo to provide the title compound (117 mg, 0.32 mmol) in 94% yield. LC-MS ESI−: 365.05 (M−1)−.

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. customReaction mixture
  4. customPrecipitate was collected
  5. washrinsed with water
  6. customIt was dried in vacuo

Sources & evidence

ORD record
ord-a568af55b28844118ee455d9cf7dd419
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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