Acetone → HCID 19391865, compound

HRID 652305Notes

Reaction equation

HRID 652305 reaction equation
[Cl:1][C:2]1[C:7]([CH:8]([CH3:10])[CH3:9])=[C:6]([Cl:11])[CH:5]=[C:4]([N+:12]([O-])=O)[C:3]=1[OH:15].[H][H].CC(C)=O>CO.[Ni]>[ClH:1].[Cl:1][C:2]1[C:7]([CH:8]([CH3:10])[CH3:9])=[C:6]([Cl:11])[CH:5]=[C:4]([NH2:12])[C:3]=1[OH:15]

Participants

6

Reactant 3

HCID 180AcetoneHCID 136510982,4-Dichloro-6-nitro-3-(propan-2-yl)phenolHCID 178418361HCID 178418361, compound

Product 1

HCID 19391865HCID 19391865, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

80 g (0.31 mole) of 2,4-dichloro-3-isopropyl-6-nitrophenol were hydrogenated in 425 ml of methanol with 5 g of Raney Ni in an autoclave at 25° to 30° C. and under 10 bar of H2. The mixture was stirred for an additional 30 minutes after hydrogen was no longer being absorbed, then the pressure was released and, after addition of 0.5 ml of hydrazine hydrate to the hydrogenation solution, the catalyst was filtered off under protective gas, washed with 50 ml of methanol, and the filtrate was acidified with 200 ml of concentrated HCl, while cooling to 15° to 20° C. The precipitated crystals were filtered off with suction, washed with 200 ml of cold acetone and dried. Crystals I obtained comprised 53.5 g of 98% pure material; this is 70% of theory. A further 11-12 g of 85 to 90% pure material was obtained by evaporation of the wash acetone, this corresponding to 15% of theory. The hydrogenation mother liquor was discarded.

Workup

  1. customwas no longer being absorbed
  2. additionafter addition of 0.5 ml of hydrazine hydrate to the hydrogenation solution
  3. filtrationthe catalyst was filtered off under protective gas
  4. washwashed with 50 ml of methanol
  5. temperaturewhile cooling to 15° to 20° C
  6. filtrationThe precipitated crystals were filtered off with suction
  7. washwashed with 200 ml of cold acetone
  8. customdried
  9. customCrystals I obtained

Sources & evidence

ORD record
ord-29e9becc02c14380945ea311ff25882d
Source dataset
uspto-grants-1987_06
Patent number
US04670608

Reaction notes

Loading…