Ammonium Hydroxide → HCID 14208513, compound

HRID 1373294Notes

Reaction equation

HRID 1373294 reaction equation
[CH2:1]([O:8][C:9]1[C:17]([O:18][CH3:19])=[CH:16][CH:15]=[C:14]([N+:20]([O-])=O)[C:10]=1[C:11]([OH:13])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[NH4+]>O>[NH2:20][C:14]1[C:10]([C:11]([OH:13])=[O:12])=[C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:17]([O:18][CH3:19])=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 142085122-(Benzyloxy)-3-methoxy-6-nitrobenzoic acid

Product 1

HCID 14208513HCID 14208513, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A solution of ferrous sulphate heptahydrate (99 g) in water (410 ml) that had been heated to 70° C. was added to a mixture of 2-benzyloxy-3-methoxy-6-nitrobenzoic acid (Bull. Soc. Chim. France, 1965, 1417; 15.5 g) and concentrated aqueous ammonium hydroxide (370 ml) which was heated to 70° C. The resultant mixture was heated to reflux for 30 minutes. The mixture was filtered and the basicity of the filtrate was adjusted to pH8 by the addition of 2N aqueous hydrochloric acid and then the filtrate was acidified to pH4 by the addition of 1M aqueous citric acid solution. The mixture was partitioned between ethyl acetate and water. The organic layer was washed with water and with brine, dried over magnesium sulphate and evaporated to give 6-amino-2-benzyloxy-3-methoxybenzoic acid (12.15 g); NMR Spectrum: (CDCl3) 3.9 (s, 3H), 5.22 (s, 2H), 6.5 (d, 1H), 7.05 (d, 1H), 7.35–7.55 (m, 5H): Mass Spectrum: M+H+ 274.

Workup

  1. temperatureto reflux for 30 minutes
  2. filtrationThe mixture was filtered
  3. additionthe basicity of the filtrate was adjusted to pH8 by the addition of 2N aqueous hydrochloric acid
  4. additionthe filtrate was acidified to pH4 by the addition of 1M aqueous citric acid solution
  5. customThe mixture was partitioned between ethyl acetate and water
  6. washThe organic layer was washed with water and with brine
  7. dry with materialdried over magnesium sulphate
  8. customevaporated

Sources & evidence

ORD record
ord-9ba138c264d04740a8863594c5bb8d70
Source dataset
uspto-grants-2007_01
Patent number
US07160891B2

Reaction notes

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