Gamma-Aminobutyric Acid → HCID 71735139, compound

HRID 1481200Notes

Reaction equation

HRID 1481200 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].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

5

Reactant 3

HCID 119Gamma-Aminobutyric AcidHCID 10942334Sodium MethoxideHCID 86709142Methyl 4-hydroxy-7-phenoxyisoquinoline-3-carboxylate

Product 1

HCID 71735139HCID 71735139, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 4-hydroxy-7-phenoxy-isoquinoline-3-carboxylic acid methyl ester (1.08 g, 3.66 mmol) in flask was added 4-Amino-butyric acid (3.77 g, 36.6 mmol) and NaOMe (58 mL, 29.28 mmol, 0.5 M solution in MeOH). The reaction mixture was allowed to reflux. After 24 h, the mixture was cooled to rt, and concentrated in vacuo to give residue as a solid. The solid was dissolved in water (50 mL), extracted with CH2Cl2 (2×20 mL). The aqueous solution was acidified by 1N HCl solution, filtered, washed with water, dried to give 1.32 g of title of the compound as a white solid: MS (m/z) 367.0 (M+1)+.

Workup

  1. temperatureto reflux
  2. concentrationconcentrated in vacuo
  3. customto give residue as a solid
  4. extractionextracted with CH2Cl2 (2×20 mL)
  5. filtrationfiltered
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-bd36d4ce8c99493291f0d28c6cddd9c2
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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