Sodium Dithionite → 2-Amino-4-(benzyloxy)-3-methoxybenzoic acid

HRID 487727Notes

Reaction equation

HRID 487727 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[C:11]([N+:18]([O-])=O)[C:10]=1[O:21][CH3:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.O.O.C([O-])(=O)C.[Na+].S(S([O-])=O)([O-])=O.[Na+].[Na+]>O>[CH2:1]([O:8][C:9]1[C:10]([O:21][CH3:22])=[C:11]([NH2:18])[C:12](=[CH:16][CH:17]=1)[C:13]([OH:15])=[O:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 24489Sodium DithioniteHCID 5618164-(Benzyloxy)-3-methoxy-2-nitrobenzoic acidHCID 23665404Sodium Acetate Trihydrate

Product 1

HCID 156628622-Amino-4-(benzyloxy)-3-methoxybenzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a vigorously stirring suspension of 4-benzyloxy-3-methoxy-2-nitrobenzoic acid (10.918 g, 0.036 mol) in water (200 ml) containing sodium acetate trihydrate (4.5 g) was added portionwise of sodium hydrosulfite (31 g, 0.18 mol) for 2 hours at 70 ° C. The reaction mixture was kept at this temperature for an additional 4 hours. After cooling, the precipitates were collected by filtration and washed with water. The product was recrystallized from ethanol to give 4-benzyloxy-3-methoxyanthranilic acid, 6.46 g (65.6%) with mp. 167-8 ° C. 1H-NMR: Analyses: Calculated for C15H15NO4 : C, 65.92; H, 5.53; N, 5.13. Found: C, 66.14; H, 5.55; N, 5.24.

Workup

  1. temperatureAfter cooling
  2. filtrationthe precipitates were collected by filtration
  3. washwashed with water
  4. customThe product was recrystallized from ethanol

Sources & evidence

ORD record
ord-311cd73b1a9146f7ad9fded0fb878a27
Source dataset
uspto-grants-1994_03
Patent number
US05296602

Reaction notes

Loading…