Sodium Hydroxide → 9-(2-fluoro-ethyl)-2,3,4,9-tetrahydro-1H-carbazole-4-carboxylic acid

HRID 628719Notes

Reaction equation

HRID 628719 reaction equation
C([O:3][C:4]([CH:6]1[C:18]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]([CH2:19][CH2:20][F:21])[C:10]=2[CH2:9][CH2:8][CH2:7]1)=[O:5])C.[OH-].[Na+]>C(O)C.O>[F:21][CH2:20][CH2:19][N:11]1[C:10]2[CH2:9][CH2:8][CH2:7][CH:6]([C:4]([OH:5])=[O:3])[C:18]=2[C:17]2[C:12]1=[CH:13][CH:14]=[CH:15][CH:16]=2

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 666792469-(2-Fluoro-ethyl)-2,3,4,9-tetrahydro-1H-carbazole-4-carboxylic acid ethyl ester

Product 1

HCID 666800789-(2-fluoro-ethyl)-2,3,4,9-tetrahydro-1H-carbazole-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

9-(2-Fluoro-ethyl)-2,3,4,9-tetrahydro-1H-carbazole-4-carboxylic acid ethyl ester (30) (380 mg, 1.3 mmol) was dissolved in ethanol (3 mL) and then NaOH (520 nm) in water (5 mL) was added The reaction was heated at reflux for 2 h. The reaction was concentrated in vacuo and the residue diluted with water and washed with dichloromethane (2×50 mL). The aqueous layer was added drop wise to 2 N HCl (50 mL) and then extracted into dichloromethane (3×50 mL).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 h
  3. concentrationThe reaction was concentrated in vacuo
  4. additionthe residue diluted with water
  5. washwashed with dichloromethane (2×50 mL)
  6. additionThe aqueous layer was added drop wise to 2 N HCl (50 mL)
  7. extractionextracted into dichloromethane (3×50 mL)

Sources & evidence

ORD record
ord-f4d17f5a0f0d40cc9aea6983caa1488c
Source dataset
uspto-grants-2016_04
Patent number
US09314541B2

Reaction notes

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