Hydrochloric Acid → 4-Hydroxy-2-methyl-7-nitro-2,3-dihydro-isoindol-1-one

HRID 604281Notes

Reaction equation

HRID 604281 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]([O:13][Si](C(C)(C)C)(C)C)[C:5]=1[CH2:21]Br.[CH3:24][NH2:25].CO.Cl>C1COCC1>[OH:13][C:6]1[CH:7]=[CH:8][C:9]([N+:10]([O-:12])=[O:11])=[C:4]2[C:5]=1[CH2:21][N:25]([CH3:24])[C:3]2=[O:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 6329MethylamineHCID 59849199HCID 59849199, compound

Product 1

HCID 598492054-Hydroxy-2-methyl-7-nitro-2,3-dihydro-isoindol-1-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

At room temperature, a solution of 2-bromomethyl-3-(tert-butyl-dimethyl-silanyloxy)-6-nitro-benzoic acid methyl ester (12.6 g, 25.1 mmol) in 60 mL of THF is added 2M solution of methylamine in THF (37.7 mL, 75.3 mmol) at 0° C. and then the reaction mixture is stirred for 6 hours at the room temperature. Methanol and 1M Hydrochloric acid solution are added to the reaction mixture. The mixture is evaporated in vacuo and the precipitate is collected to give 4-hydroxy-2-methyl-7-nitro-2,3-dihydro-isoindol-1-one (2.1 g) as yellow solid in 40% yields for 3 steps.

Workup

  1. customThe mixture is evaporated in vacuo
  2. customthe precipitate is collected

Sources & evidence

ORD record
ord-47e52a19da0547719a7a33603c88b723
Source dataset
uspto-grants-2011_03
Patent number
US07910585B2

Reaction notes

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