Ammonium Chloride → Methyl 2-amino-3-methyl-5-nitrobenzoate

HRID 2216201Notes

Reaction equation

HRID 2216201 reaction equation
[CH3:1][C:2]1[C:7]2[NH:8][C:9](=O)[O:10][C:11](=[O:12])[C:6]=2[CH:5]=[C:4]([N+:14]([O-:16])=[O:15])[CH:3]=1.C[O-].[Na+].[NH4+].[Cl-]>CO>[CH3:9][O:10][C:11](=[O:12])[C:6]1[CH:5]=[C:4]([N+:14]([O-:16])=[O:15])[CH:3]=[C:2]([CH3:1])[C:7]=1[NH2:8]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 10942334Sodium MethoxideHCID 218865708-methyl-6-nitro-2,4-dihydro-1H-3,1-benzoxazine-2,4-dione

Product 1

HCID 45089339Methyl 2-amino-3-methyl-5-nitrobenzoateYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a suspension of 8-methyl-6-nitro-1H-benzo[d][1,3]oxazine-2,4-dione ((Example 295: step b) 1.04 g, 4.68 mmol) in methanol (30 mL) was added a solution of sodium methoxide (0.5 M, 0.94 mL, 4.7 mmol) in methanol. The mixture was stirred at ambient temperature for 1 hour and neutralized by addition of saturated NH4Cl. Methanol was removed under reduced pressure and the resulting mixture was filtered. The solids were washed with H2O (twice), dried in high vacuum to give the product (0.97 g, 99% yield) as a yellow solid. 1H NMR (DMSO) δ 8.48 (d, 1H, J=2.7 Hz), 8.02–8.01 (m, 1H), 7.75 (br s, 2H), 3.86 (s, 3H), 2.20 (s, 3H).

Workup

  1. customMethanol was removed under reduced pressure
  2. filtrationthe resulting mixture was filtered
  3. washThe solids were washed with H2O (twice),
  4. customdried in high vacuum

Sources & evidence

ORD record
ord-5522486582bc47ae932aa18e711de755
Source dataset
uspto-grants-2006_09
Patent number
US07109354B2

Reaction notes

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