Methanol → HCID 19858589, compound

HRID 1906060Notes

Reaction equation

HRID 1906060 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][C:12]=2[Cl:21])=[CH:6][C:5]=1[NH:22][CH2:23][CH2:24][CH2:25][C:26]([OH:28])=[O:27])([O-:3])=[O:2].S(=O)(=O)(O)O.[OH-].[Na+].[CH3:36]O>>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:18])([F:19])[F:20])=[CH:13][C:12]=2[Cl:21])=[CH:6][C:5]=1[NH:22][CH2:23][CH2:24][CH2:25][C:26]([O:28][CH3:36])=[O:27])([O-:3])=[O:2]

Participants

5

Reactant 4

HCID 887MethanolHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 19858600HCID 19858600, compound

Product 1

HCID 19858589HCID 19858589, compound

Procedure

8 g of N-[2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenyl]-4-amino-n-butyric acid are dissolved in 50 ml of methanol and then 10 ml of concentrated sulfuric acid are slowly added. The reaction mixture is left to stand for some hours, then poured onto ice, made alkaline with sodium hydroxide solution and extracted with toluene. The toluene extract is washed with water until neutral and substantially concentrated in vacuo. The residue is crystallised from hexane, affording 6 g of methyl N-[2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenyl]-4-amino-n-butyrate with a melting point of 60°-62° C.

Workup

  1. waitThe reaction mixture is left
  2. waitto stand for some hours
  3. additionpoured onto ice
  4. extractionextracted with toluene
  5. extractionThe toluene extract
  6. washis washed with water until neutral and
  7. concentrationsubstantially concentrated in vacuo
  8. customThe residue is crystallised from hexane

Sources & evidence

ORD record
ord-3e03a43900354c89a3640d7442910974
Source dataset
uspto-grants-1987_03
Patent number
US04649212

Reaction notes

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