Hydrochloric Acid → HCID 54370809, compound

HRID 261514Notes

Reaction equation

HRID 261514 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[C:3]=1[NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11](=[O:16])[C:12]([O:14][CH3:15])=[O:13].[BH4-].[Na+].Cl>C(O)C.O>[Cl:1][C:2]1[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[C:3]=1[NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH:11]([OH:16])[C:12]([O:14][CH3:15])=[O:13]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 54013338HCID 54013338, compound

Product 1

HCID 54370809HCID 54370809, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 6.5 g of methyl 2-(2,6-dichloroanilino)phenylglyoxylate in 130 ml of ethanol was added 0.5 g of sodium borohydride while cooling at -15° to -20° C., and the mixture was stirred at 0° C. for 2 hours and then at room temperature for further 1 hour. Thereafter, the reaction mixture was mixed with diluted hydrochloric acid for decomposition, diluted with 500 ml of water and extracted with ether. The ether extract was washed with water, dried over anhydrous sodium sulfate and then concentrated without heating. The resulting residue was recrystallized from ethanol to give 6.2 g of methyl 2-(2,6-dichloroanilino)phenylglycolate. m.p. 123°-124° C. Yield: 95% of theoretical amount

Workup

  1. temperaturewhile cooling at -15° to -20° C.
  2. waitat room temperature for further 1 hour
  3. extractionextracted with ether
  4. extractionThe ether extract
  5. washwas washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. temperaturewithout heating
  9. customThe resulting residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-033caa16f83348c6a01da83b0394598d
Source dataset
uspto-grants-1979_08
Patent number
US04166128

Reaction notes

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