Methylamine → HCID 86687928, compound

HRID 2401473Notes

Reaction equation

HRID 2401473 reaction equation
Br[CH2:2][C:3]1[C:12]([O:13][CH3:14])=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=[CH:9][C:4]=1[C:5](OC)=[O:6].C[CH2:19][N:20](CC)CC.CN>CO>[CH3:14][O:13][C:12]1[C:11]([N+:15]([O-:17])=[O:16])=[CH:10][CH:9]=[C:4]2[C:3]=1[CH2:2][N:20]([CH3:19])[C:5]2=[O:6]

Participants

5

Reactant 3

HCID 6329MethylamineHCID 8471TriethylamineHCID 86687927HCID 86687927, compound

Product 1

HCID 86687928HCID 86687928, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of methyl 2-(bromomethyl)-3-methoxy-4-nitrobenzoate (300 mg, 1.0 mmol) in MeOH (10 mL) was added Et3N (120 mg, 1.2 mmol) and CH3NH2 (1.0 mL, 4M in MeOH). The solution was stirred at 70° C. for 4 h. The solvent was evaporated in vacuo, and the residue was purified by silica gel-column (eluting with PE/EA=10:1) to afford 4-methoxy-2-methyl-5-nitroisoindolin-1-one as a yellow solid (110 mg, yield 50%). m/z (ES+APCI)+: [M+H]+223.1.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residue was purified by silica gel-column (eluting with PE/EA=10:1)

Sources & evidence

ORD record
ord-7623e0db78dd450f934302243f50c35e
Source dataset
uspto-grants-2014_08
Patent number
US08796296B2

Reaction notes

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