Hydrochloric Acid → 6-Fluoro-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid
Reaction equation
C([O:3][C:4]([CH:6]1[CH2:18][C:17]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([F:19])[CH:15]=3)[NH:10][C:9]=2[CH2:8][CH2:7]1)=[O:5])C.[OH-].[K+].Cl.O>C(O)C>[F:19][C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9]1[CH2:8][CH2:7][CH:6]([C:4]([OH:5])=[O:3])[CH2:18][C:17]2=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 42.5 °C
Procedure
6-Fluoro-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid ethyl ester (80 g, 0.3 mol) was dissolved in 1 L of ethanol solution of KOH (28 g, 0.5 mol). The resulting mixture was stirred under nitrogen at 40-45° C. until completion of hydrolysis (TLC, HPLC) in 3 hrs. To the cooled solution were added 0.5 L of 1N aqueous HCl and 0.5 L of water; the resulting mixture was concentrated under reduced pressure. The target compound crystallized out of the aqueous solution when ethanol boiled out; 71.2 g (99%) of the title compound were obtained after drying.
Workup
- concentrationthe resulting mixture was concentrated under reduced pressure
- customThe target compound crystallized out of the aqueous solution when ethanol
Sources & evidence
- ORD record
- ord-40490fcd22d649f79427f1c108fc8e01
- Source dataset
- uspto-grants-2007_11
- Patent number
- US07297704B2
Reaction notes
Loading…