Sodium Hydroxide → 4-(2-Fluorophenyl)-7-morpholino-9H-pyrido[3,4-b]indole-1-carboxylic acid

HRID 2361240Notes

Reaction equation

HRID 2361240 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:20]2[C:19]3[C:14](=[CH:15][C:16]([N:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)=[CH:17][CH:18]=3)[NH:13][C:12]=2[C:11]([C:27]([O:29]CC)=[O:28])=[N:10][CH:9]=1.[OH-].[Na+]>CO>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:20]2[C:19]3[C:14](=[CH:15][C:16]([N:21]4[CH2:22][CH2:23][O:24][CH2:25][CH2:26]4)=[CH:17][CH:18]=3)[NH:13][C:12]=2[C:11]([C:27]([OH:29])=[O:28])=[N:10][CH:9]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67994836Ethyl 4-(2-fluorophenyl)-7-morpholino-9H-pyrido[3,4-b]indole-1-carboxylate

Product 1

HCID 679946914-(2-Fluorophenyl)-7-morpholino-9H-pyrido[3,4-b]indole-1-carboxylic acidYield 77%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl 4-(2-fluorophenyl)-7-morpholino-9H-pyrido[3,4-b]indole-1-carboxylate (94 mg, 0.224 mmol) in MeOH (5 mL) at room temperature was added 1N sodium hydroxide solution (1.121 mL, 1.121 mmol). The mixture was heated at reflux for 1 hr and then concentrated under vacuum. To the residue was added water (20 mL), and the resulting mixture was neutralized with 1 N HCl solution to pH 5. The precipitating product (68 mg, 0.172 mmol, 77% yield) was collected as a tan solid by suction filtration and dried at 50° C. under vacuum.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 1 hr
  3. concentrationconcentrated under vacuum
  4. additionTo the residue was added water (20 mL)

Sources & evidence

ORD record
ord-796276141b694bafae8079efac86024e
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Reaction notes

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