1-Fluoro-2-nitrobenzene → Benzenamine, N-methyl-2-nitro-

HRID 2293111Notes

Reaction equation

HRID 2293111 reaction equation
Cl.[CH3:2][NH2:3].[Na].F[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N+:12]([O-:14])=[O:13]>C1COCC1>[CH3:2][NH:3][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N+:12]([O-:14])=[O:13]

Participants

5

Procedure

Methylamine hydrochloride (2.7 g) and a 10% aqueous solution of sodium hydroxyde (30 ml) were added to a solution of 1-fluoro-2-nitrobenzene (2.82 g) in THF (20 ml). The mixture was kept at 23° for 24 h. The reaction mixture was then concentrated in vacuo, taken up with 10% aqueous sodium hydroxide (30 ml) and extracted with EA (3×30 ml). The combined organic layers were washed with a saturated ammonium chloride solution (50 ml), brine (50 ml) and dried. Evaporation of the solvent gave the title compound as an orange oil (2.894 g).

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. extractionextracted with EA (3×30 ml)
  3. washThe combined organic layers were washed with a saturated ammonium chloride solution (50 ml), brine (50 ml)
  4. customdried
  5. customEvaporation of the solvent

Sources & evidence

ORD record
ord-fe1565a7fa9242fab8b27da25e0bd0c6
Source dataset
uspto-grants-1997_11
Patent number
US05686449

Reaction notes

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