1-Butanol → HCID 22752968, compound

HRID 2163568Notes

Reaction equation

HRID 2163568 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[C:5]1[C:6](=[CH:8][CH:9]=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=1)[NH2:7])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:22](O)[CH2:23]CC>>[CH2:1]([O:3][C:4](=[O:15])[C:5]1[C:6](=[CH:8][CH:9]=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=1)[NH2:7])[CH2:2][CH2:22][CH3:23]

Participants

4

Reactant 3

HCID 2631-ButanolHCID 11430Potassium CarbonateHCID 254802Ethyl 2-amino-5-nitrobenzoate

Product 1

HCID 22752968HCID 22752968, compoundYield 93%

Conditions

Temperature
0 °C

Procedure

210 parts of 5-nitroanthranilic acid ethyl ester, 210 parts of n-butanol and 10 parts of potassium carbonate are refluxed for half an hour. The thus formed ethanol is then distilled off over a column. Distillation is continued until the boiling point of n-butanol is reached. 450 parts of cyclohexane are then added, and after addition of 4 parts each of bleaching earth and active charcoal the hot mixture is filtered, followed by cooling to 0° C. The reaction lasts for about 4 hours. The precipitate is filtered off, washed with about 100 parts of cyclohexane and dried in vacuo at 60° C. There are obtained 222 parts of 5-nitroanthranilic acid-n-butyl ester, melting point 91°-93° C. The yield is approximately 93% of the theory.

Workup

  1. distillationThe thus formed ethanol is then distilled off over a column
  2. distillationDistillation
  3. addition450 parts of cyclohexane are then added
  4. additionafter addition of 4 parts
  5. filtrationis filtered
  6. filtrationThe precipitate is filtered off
  7. washwashed with about 100 parts of cyclohexane
  8. customdried in vacuo at 60° C

Sources & evidence

ORD record
ord-c7565193013447a4bf1126c08f20ee5a
Source dataset
uspto-grants-1979_01
Patent number
US04135050

Reaction notes

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