Hydrochloric Acid → HCID 53673654, compound

HRID 247092Notes

Reaction equation

HRID 247092 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=O)([O-:3])=[O:2].[C:12]([O:18][CH:19]([CH3:22])[CH2:20][Cl:21])(=[O:17])[CH2:13][C:14]([CH3:16])=[O:15].Cl>C1(C)C=CC=CC=1>[C:14]([C:13](=[CH:7][C:6]1[CH:9]=[CH:10][CH:11]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)[C:12]([O:18][CH:19]([CH3:22])[CH2:20][Cl:21])=[O:17])(=[O:15])[CH3:16]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 74493-NitrobenzaldehydeHCID 10559247HCID 10559247, compound

Product 1

HCID 53673654HCID 53673654, compoundYield 82.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution containing 12.2 g of 3-nitrobenzaldehyde and 14.3 g of 1-methyl-2-chloroethyl acetoacetate in 80 ml of toluene, maintained at 0°-5° C., was saturated with hydrogen chloride gas. After two days at 20°-25° C., the residual hydrogen chloride was removed by bubbling nitrogen through the solution. The toluene was then evaporated off in vacuo. The residual oil was dissolved in dichloromethane and the solution thus obtained was washed with water until it was neutral. The organic phase which was separated and dried, was then evaporated to dryness under vacuum at 20° C. The residue was crystallized from 200 ml of isopropanol to give 20.70 g of the title compound, melting at 95°-96° C.

Workup

  1. temperaturemaintained at 0°-5° C.
  2. customthe residual hydrogen chloride was removed
  3. customby bubbling nitrogen through the solution
  4. customThe toluene was then evaporated off in vacuo
  5. dissolutionThe residual oil was dissolved in dichloromethane
  6. customthe solution thus obtained
  7. washwas washed with water until it
  8. customThe organic phase which was separated
  9. customdried
  10. customwas then evaporated to dryness under vacuum at 20° C
  11. customThe residue was crystallized from 200 ml of isopropanol

Sources & evidence

ORD record
ord-938cadd8fddb4a9a852aa79def21f2eb
Source dataset
uspto-grants-1987_11
Patent number
US04705797

Reaction notes

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