N-methyl-2-pyrrolidone → 6-Fluorobenzo[b]thiophen-3-amine
Reaction equation
COC([C:5]1[S:9][C:8]2[CH:10]=[C:11]([F:14])[CH:12]=[CH:13][C:7]=2[C:6]=1[NH2:15])=O.CN1CCNCC1.CN1CCCC1=O>O>[NH2:15][C:6]1[C:7]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][C:8]=2[S:9][CH:5]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 176 °C
Procedure
A mixture of methyl-6-fluoro-3-aminobenzo[b]thiophene-2-carboxylate (20.1 g), 1-methylpiperazine (13.1 g), and 1-methyl-2-pyrrolidinone (100 ml) was heated at 176° C. for 2 hrs, under nitrogen. The solution was diluted with water (400 ml) and extracted with ether. The combined extracts were washed with water, brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure to give 9.32 g of 3-amino-6-fluorobenzo[b]thiophene.
Workup
- extractionextracted with ether
- washThe combined extracts were washed with water, brine
- dry with materialdried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationthe filtrate was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-e4d6c3bc1cd642f292d51b89930cb6c3
- Source dataset
- uspto-grants-1993_07
- Patent number
- US05225412
Reaction notes
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