Methyl 5-(2,4-dimethoxybenzylamino)-4-nitrothiophene-2-carboxylate → Methyl 5-amino-4-nitrothiophene-2-carboxylate
Reaction equation
COC1C=C(OC)C=CC=1C[NH:6][C:7]1[S:11][C:10]([C:12]([O:14][CH3:15])=[O:13])=[CH:9][C:8]=1[N+:16]([O-:18])=[O:17]>C(Cl)Cl.C(O)(C(F)(F)F)=O>[NH2:6][C:7]1[S:11][C:10]([C:12]([O:14][CH3:15])=[O:13])=[CH:9][C:8]=1[N+:16]([O-:18])=[O:17]Participants
4
Procedure
A solution of methyl 5-(2,4-dimethoxybenzylamino)-4-nitrothiophene-2-carboxylate 86 (40.3 mmol, 14.2 g) in CH2Cl2 (100 mL) and TFA (10 mL) was stirred overnight at rt. Reaction mixture was poured on ice and the precipitate was collected to give methyl 5-amino-4-nitrothiophene-2-carboxylate 87 (8.15 g, 100%). NMR (400 MHz, DMSO-d6) 3.77 (s, 3H), 7.75 (s, 1H), 9.06 (br s, 2H).
Workup
- customReaction mixture
- additionwas poured on ice
- customthe precipitate was collected
Sources & evidence
- ORD record
- ord-3e4ee040543d4e9fb457956a0816bcf5
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08669256B2
Reaction notes
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