Benzyl Chloride → 2-Amino-5-(benzyloxy)benzamide

HRID 1395800Notes

Reaction equation

HRID 1395800 reaction equation
[OH:1][C:2]1[CH:10]=[C:6]([C:7]([NH2:9])=[O:8])[C:5]([NH2:11])=[CH:4][CH:3]=1.[OH-].[Na+].[CH2:14](Cl)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>O>[CH2:14]([O:1][C:2]1[CH:10]=[C:6]([C:7]([NH2:9])=[O:8])[C:5]([NH2:11])=[CH:4][CH:3]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 14798Sodium HydroxideHCID 120149202-Amino-5-hydroxybenzamide

Product 1

HCID 203381422-Amino-5-(benzyloxy)benzamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5-hydroxyanthranilamide (15.2 g), 250 ml water, 5.1 ml 50% NaOH, and 11.7 ml benzyl chloride was heated 1/2 hour at 95°, filtered and the solid recrystallized from 200 ml butanol to give 16.6 g product, m.163-5.

Workup

  1. temperaturewas heated 1/2 hour at 95°
  2. filtrationfiltered
  3. customthe solid recrystallized from 200 ml butanol

Sources & evidence

ORD record
ord-5b81374c4c1e49008aa9c37e3b8e322d
Source dataset
uspto-grants-1980_05
Patent number
US04205173

Reaction notes

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