Methyl 5-(2,4-dimethoxybenzylamino)-4-nitrothiophene-2-carboxylate → Methyl 5-amino-4-nitrothiophene-2-carboxylate

HRID 1184895Notes

Reaction equation

HRID 1184895 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

Reactant 1

HCID 67125578Methyl 5-(2,4-dimethoxybenzylamino)-4-nitrothiophene-2-carboxylate

Product 1

HCID 20330731Methyl 5-amino-4-nitrothiophene-2-carboxylateYield 100%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

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

  1. customReaction mixture
  2. additionwas poured on ice
  3. 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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