Methylamine → 4-Fluoro-2-methyl-7-nitroisoindolin-1-one

HRID 604264Notes

Reaction equation

HRID 604264 reaction equation
C[O:2][C:3](=O)[C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[C:6]([F:13])[C:5]=1[CH2:14]Br.[CH3:17][NH2:18]>C1COCC1>[F:13][C:6]1[CH:7]=[CH:8][C:9]([N+:10]([O-:12])=[O:11])=[C:4]2[C:5]=1[CH2:14][N:18]([CH3:17])[C:3]2=[O:2]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 598492172-Bromomethyl-3-fluoro-6-nitro-benzoic acid methyl ester

Product 1

HCID 598492024-Fluoro-2-methyl-7-nitroisoindolin-1-oneYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

At room temperature, a solution of 2-bromomethyl-3-fluoro-6-nitro-benzoic acid methyl ester (4.48 g, 15.3 mmol) in THF (100 mL) is treated with 2M solution of methylamine in THF (23 mL, 46 mmol), and the mixture is stirred for 48 h at the room temperature. The reaction mixture is filtrated through a glass filter and the precipitates are collected and washed with ethyl acetate. The filtrate is washed with sat. aqueous solution of NaHCO3 and brine, dried over Na2SO4, and concentrated under reduced pressure to give 4-fluoro-2-methyl-7-nitro-2,3-dihydro-isoindol-1-one (1.6 g, 7.61 mmol 50%) as yellow solids. 1H-NMR (400 MHz, δ, ppm) CDCl3: 3.22 (s, 3H), 4.47 (s, 2H), 7.32 (dd, 1H), 7.84 (dd, 1H).

Workup

  1. filtrationThe reaction mixture is filtrated through a glass
  2. filtrationfilter
  3. customthe precipitates are collected
  4. washwashed with ethyl acetate
  5. washThe filtrate is washed with sat. aqueous solution of NaHCO3 and brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d929773e96f9447085aafb132f51283f
Source dataset
uspto-grants-2011_03
Patent number
US07910585B2

Reaction notes

Loading…