Methyl 5-fluoro-3-methyl-2-nitrobenzoate → Methyl 2-amino-5-fluoro-3-methylbenzoate

HRID 2168507Notes

Reaction equation

HRID 2168507 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH3:15])[C:5]([N+:12]([O-])=O)=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]>CO.[Pd]>[NH2:12][C:5]1[C:4]([CH3:15])=[CH:3][C:2]([F:1])=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8]

Participants

4

Reactant 1

HCID 53415166Methyl 5-fluoro-3-methyl-2-nitrobenzoate

Product 1

HCID 53415135Methyl 2-amino-5-fluoro-3-methylbenzoateYield 94.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of methyl 5-fluoro-3-methyl-2-nitrobenzoate (8.4 g, 39.4 mmol) from Step B above in methanol (150 mL) was purged with nitrogen. Palladium on charcoal was added to the solution and hydrogenation was carried out for 24 h at 1 atm. The reaction mixture was filtered through a pad of Celite and washed with methanol. The filtrate was concentrated in vacuo to afford methyl 2-amino-5-fluoro-3-methylbenzoate (6.8 g, 94%) as a white solid. 1H NMR (500 MHz, DMSO-d6) δ 7.32 (dd, J=10.0, 3.0 Hz, 1H), 7.17 (dd, J=9.0, 3.0 Hz, 1H), 6.40 (s, 2H), 3.80 (s, 3H), 2.13 (s, 3H); MS (ESI+) m/z 184 (M+H).

Workup

  1. filtrationThe reaction mixture was filtered through a pad of Celite
  2. washwashed with methanol
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-d5ac0467304a4da788cbab0f8aa8ce79
Source dataset
uspto-grants-2015_06
Patent number
US09045501B2

Reaction notes

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