Methyl 5-methyl-4-nitrothiophene-2-carboxylate → methyl (E)-5-(2-dimethylaminovinyl)-4-nitrothiophene-2-carboxylate

HRID 1008986Notes

Reaction equation

HRID 1008986 reaction equation
[CH3:1][C:2]1[S:6][C:5]([C:7]([O:9][CH3:10])=[O:8])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].COO[CH:17](OOC)[N:18]([CH3:20])[CH3:19]>CN(C=O)C>[CH3:17][N:18]([CH3:20])/[CH:19]=[CH:1]/[C:2]1[S:6][C:5]([C:7]([O:9][CH3:10])=[O:8])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12]

Participants

4

Reactant 2

HCID 268679Methyl 5-methyl-4-nitrothiophene-2-carboxylateHCID 23441001Dimethylformamide dimethoxyacetal

Product 1

HCID 12110978methyl (E)-5-(2-dimethylaminovinyl)-4-nitrothiophene-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 0.3M solution of methyl 5-methyl-4-nitrothiophene-2-carboxylate in dry DMF was treated with N,N-dimethylformamide dimethoxy acetal (10 eq.) overnight at 110° C. Evaporation to dryness gave a residue that was used as such. 1H-NMR (300 MHz, CDCl3, 300 K, δ) 8.32 (s, 1H), 7.53 (d, 1H, J 13.4), 6.77 (d, 1H, J 13.4), 4.08 (s, 3H), 3.29 (s, 6H); MS (ES+) m/z 257 (M+H)+.

Workup

  1. customEvaporation to dryness
  2. customgave a residue that

Sources & evidence

ORD record
ord-3326c0875b1447a5a46997da72331f15
Source dataset
uspto-grants-2011_07
Patent number
US07973026B2

Reaction notes

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