Hydrochloric Acid → HCID 21465919, compound

HRID 1940198Notes

Reaction equation

HRID 1940198 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:18]([O-:20])=[O:19])=[C:6]([CH:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[Cl:17])[CH:9]=O)[CH:7]=1.Cl.[CH3:22][O:23][C:24](=[O:27])[CH2:25][NH2:26].C([O-])(=O)C.[Na+].C([BH3-])#N.[Na+].Cl.[OH-].[Na+]>CO>[CH3:22][O:23][C:24](=[O:27])[CH2:25][NH:26][CH2:9][CH:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[Cl:17])[C:6]1[CH:7]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=1[N+:18]([O-:20])=[O:19]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 122755Glycine methyl ester hydrochlorideHCID 517045Sodium AcetateHCID 5003444Sodium cyanoborohydrideHCID 53926694HCID 53926694, compound

Product 1

HCID 21465919HCID 21465919, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of α-(5-chloro-2-nitrophenyl)-2-chlorophenylacetaldehyde (1.68 g) in methanol(15 ml) were added glycine methyl ester hydrochloride (0.69 g) and sodium acetate (0.45 g). The mixture was stirred for 30 minutes at room temperature, to which was added sodium cyanoborohydride (0.35 g). To this mixture was added hydrogen chloride for 5 minutes. This mixture solution was stirred for 3 hours at 50° C., to which was added a 1N aqueous solution of sodium hydroxide (50 ml), followed by extraction with dichloromethane. The extract solution was washed with water, then the solvent was distilled off. The residual oily product was purified by means of a silica-gel column chromatography (hexane:acetic acid ethyl ester=3:1 v/v as an eluent) to give 1.1 g of an oily compound.

Workup

  1. stirringThis mixture solution was stirred for 3 hours at 50° C., to which
  2. extractionfollowed by extraction with dichloromethane
  3. washThe extract solution was washed with water
  4. distillationthe solvent was distilled off
  5. customThe residual oily product was purified by means of a silica-gel column chromatography (hexane

Sources & evidence

ORD record
ord-63af6e09da2941c1bdc583afd011c97f
Source dataset
uspto-grants-1997_12
Patent number
US05698691

Reaction notes

Loading…