Water → HCID 19068987, compound

HRID 1957198Notes

Reaction equation

HRID 1957198 reaction equation
[CH3:1][N:2]1[C:12]2[C:7](=[C:8]([Cl:14])[CH:9]=[C:10]([Cl:13])[CH:11]=2)[C:5](=O)[C:3]1=[O:4].NN.[Na].O>C(O)C>[CH3:1][N:2]1[C:12]2[C:7](=[C:8]([Cl:14])[CH:9]=[C:10]([Cl:13])[CH:11]=2)[CH2:5][C:3]1=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 9321HydrazineHCID 5360545SodiumHCID 185185371-Methyl-4,6-dichloroisatin

Product 1

HCID 19068987HCID 19068987, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

1-Methyl-4,6-dichloroisatin (4.0 g) was suspended in dry ethanol (40 ml), hydrazine (9 ml) was added and the mixture was refluxed in 6 h. The mixture was then added slowly at 70° C. to a solution of sodium (1.74 g) in dry ethanol (80 ml) and refluxed overnight. The reaction mixture was cooled to room temperature, water (50 ml) was added and the volume was reduced to about one third by evaporation. The mixture was then poured onto icewater (1000 ml) and acidified with 6M HCl (pH=1). The precipitate was filtered off washed with water and dried to afford 3.27 g (87%) of (43). M.p. 144°-145° C.

Workup

  1. temperaturethe mixture was refluxed in 6 h
  2. temperaturerefluxed overnight
  3. customthe volume was reduced to about one third by evaporation
  4. additionThe mixture was then poured onto icewater (1000 ml)
  5. filtrationThe precipitate was filtered off
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-65d519d84f37453d9e26d8737947d57a
Source dataset
uspto-grants-1998_07
Patent number
US05783575

Reaction notes

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