Potassium Hydroxide → HCID 21440126, compound

HRID 328959Notes

Reaction equation

HRID 328959 reaction equation
[C:1]([C:9]1[C:17]([N+:18]([O-])=O)=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[CH:11][C:10]=1[O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.NN.[OH-].[K+]>O.C(O)COCCO>[NH2:18][C:17]1[C:9]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[C:10]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:11]=[C:12]([CH:16]=1)[C:13]([OH:15])=[O:14]

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 21440223HCID 21440223, compound

Product 1

HCID 21440126HCID 21440126, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8117Diethylene GlycolSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 4-benzoyl-3-benzyloxy-5-nitrobenzoic acid (2.7 g), 98% aqueous hydrazine hydrate (4.5 ml), potassium hydroxide (1.5 g) in water (3.0 ml) and di-ethylene glycol (20 ml) is stirred at about 130° C. for 1 hour. The temperature is then slowly raised to 215° C. allowing volatile material to distil off. The stirring at 215° C. is continued for a further 2-3 hours until the nitrogen evolution has ceased. After cooling and dilution with water (30 ml), the resulting solution is acidified with conc. hydrochloric acid (3 ml). The resulting precipitate is collected by filtration and washed with water. After drying and recrystallization twice from 96% ethanol, 5-amino-4-benzyl-3-benzyloxybenzoic acid is obtained with a melting point of 207.5° -209.5° C.

Workup

  1. temperatureThe temperature is then slowly raised to 215° C.
  2. customto distil off
  3. waitThe stirring at 215° C. is continued for a further 2-3 hours until the nitrogen evolution
  4. temperatureAfter cooling
  5. filtrationThe resulting precipitate is collected by filtration
  6. washwashed with water
  7. customAfter drying
  8. customrecrystallization twice from 96% ethanol

Sources & evidence

ORD record
ord-7e44ee2f6bd3435b9d348c62981a5b30
Source dataset
uspto-grants-1977_04
Patent number
US04018794

Reaction notes

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