Methylamine → 5-Chloro-4-fluoro-N-methyl-2-nitrobenzenamine

HRID 1048970Notes

Reaction equation

HRID 1048970 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([N+:9]([O-:11])=[O:10])=[C:4](F)[CH:3]=1.C[CH2:14][N:15](C(C)C)C(C)C.CN>CN(C=O)C>[Cl:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([N+:9]([O-:11])=[O:10])=[C:4]([CH:3]=1)[NH:15][CH3:14]

Participants

5

Reactant 3

HCID 6329MethylamineHCID 81531DiisopropylethylamineHCID 157514831-Chloro-2,5-difluoro-4-nitrobenzene

Product 1

HCID 666842915-Chloro-4-fluoro-N-methyl-2-nitrobenzenamine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-chloro 2,5-difluoro nitrobenzene (2.0 g, 0.010 mol) in DMF (15 ml) was added DIPEA (4.5 ml, 0.026 mol) followed by MeNH2 (5 ml, 0.010 mol, 2M in THF) and the resulting solution was stirred at room temperature for 12 h. The reaction was quenched with H2O and extracted with EtOAc (3×30 ml). The combined organic layers were washed with brine dried over Na2SO4 and concentrated under vacuum to get crude product which was purified column chromatography to get the title compound 5-chloro-4-fluoro-N-methyl-2-nitroaniline as a yellow solid, 1H NMR (400 MHz, DMSO-d6), δ: 8.20 (s, 1H), 8.09 (d, J=10 Hz, 1H), 7.22-7.20 (d, J=6.4 Hz, 1H), 2.95 (s, 3H). MS (M+1): 205.12

Workup

  1. customThe reaction was quenched with H2O
  2. extractionextracted with EtOAc (3×30 ml)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under vacuum
  6. customto get crude product which
  7. customwas purified column chromatography

Sources & evidence

ORD record
ord-50a4c41885504c139518c41eb9997b62
Source dataset
uspto-grants-2016_07
Patent number
US09382226B2

Reaction notes

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