2-Methoxy-4-nitroaniline → Thiophene, 2-(2-methoxy-4-nitrophenyl)-

HRID 2290550Notes

Reaction equation

HRID 2290550 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:4]=1N.[S:13]1[CH:17]=[CH:16][CH:15]=[CH:14]1.C(ON=O)(C)(C)C>[Cu]>[CH3:1][O:2][C:3]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:4]=1[C:14]1[S:13][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 73372-Methoxy-4-nitroanilineHCID 8030ThiopheneHCID 10906Tert-Butyl nitrite

Product 1

HCID 13768627Thiophene, 2-(2-methoxy-4-nitrophenyl)-Yield 53.6%

Reagents, catalysts & solvents 1

HCID 23978CopperCatalyst

Conditions

Temperature
55 °C

Procedure

A stirred mixture of 38.1 g (0.23 mole) of 2-methoxy-4-nitroaniline and 38.1 g (0.6 mole) of copper powder in 953.0 g (11.33 mole) of thiophene was heated at 55° C. During a 1.1 hour period 40.5 ml (0.34 mole) of t-butylnitrite was added to the warm reaction mixture. After complete addition the mixture was heated at 70° C. for approximately 18 hours then cooled to room temperature. The solvent was removed from the reaction mixture by distillation under reduced pressure to leave a residue. The residue was purified by column chromatography on silica gel, eluting with heptane:toluene (25:75), to yield 29.0 g of 2-(2-methoxy-4-nitrophenyl)thiophene.

Workup

  1. additionAfter complete addition the mixture
  2. temperaturewas heated at 70° C. for approximately 18 hours
  3. temperaturethen cooled to room temperature
  4. customThe solvent was removed from the reaction mixture by distillation under reduced pressure
  5. customto leave a residue
  6. customThe residue was purified by column chromatography on silica gel
  7. washeluting with heptane:toluene (25:75)

Sources & evidence

ORD record
ord-c090a449936f4bf486d5cb91a515da94
Source dataset
uspto-grants-1986_10
Patent number
US04617316

Reaction notes

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