Allyl 2-methyl-6-nitrobenzoate → Allyl 2-amino-6-methylbenzoate

HRID 1736362Notes

Reaction equation

HRID 1736362 reaction equation
[CH3:1][C:2]1[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-])=O)[C:3]=1[C:4]([O:6][CH2:7][CH:8]=[CH2:9])=[O:5]>CO>[NH2:14][C:10]1[CH:11]=[CH:12][CH:13]=[C:2]([CH3:1])[C:3]=1[C:4]([O:6][CH2:7][CH:8]=[CH2:9])=[O:5]

Participants

3

Reactant 1

HCID 19432516Allyl 2-methyl-6-nitrobenzoate

Product 1

HCID 19432484Allyl 2-amino-6-methylbenzoateYield 75%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Stannous chloride dihydrate (15.3 g, 67.8 mM) was suspended in methanol (25 ml), and a solution of allyl 2-methyl-6-nitrobenzoate (3.0 g, 13.6 mM) in methanol (5 ml) was added. The mixture was heated at reflux for 1 hour, cooled, and solvent removed. The residue was treated with ethyl acetate (100 ml), made basic with 880 ammonia and diluted with water (50 ml). The organic layer was decanted from the slurry of tin salts, which was extracted with two further portions of ethyl acetate. The combined organic extracts were washed with dilute ammonia, water, brine, and dried over MgSO4, to give allyl 2-amino-6-methylbenzoate as an oil (1.94 g, 75%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 1 hour
  3. temperaturecooled
  4. customsolvent removed
  5. additionThe residue was treated with ethyl acetate (100 ml)
  6. additiondiluted with water (50 ml)
  7. customThe organic layer was decanted from the slurry of tin salts, which
  8. extractionwas extracted with two further portions of ethyl acetate
  9. washThe combined organic extracts were washed with dilute ammonia, water, brine
  10. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-a6a9c3170fca4416b242b4f60ca75e49
Source dataset
uspto-grants-1996_07
Patent number
US05541178

Reaction notes

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