Water → HCID 21521295, compound

HRID 918220Notes

Reaction equation

HRID 918220 reaction equation
[Br-:1].[CH3:2][N+:3]1([CH3:25])[C:12]2[C:7](=[C:8]([N:17]=NC3C=CC=CC=3)[CH:9]=[C:10]([CH2:14][CH2:15][CH3:16])[C:11]=2[OH:13])[CH2:6][CH2:5][CH2:4]1.O.[H][H]>[Pd].CO>[Br-:1].[CH3:25][N+:3]1([CH3:2])[C:12]2[C:7](=[C:8]([NH2:17])[CH:9]=[C:10]([CH2:14][CH2:15][CH3:16])[C:11]=2[OH:13])[CH2:6][CH2:5][CH2:4]1

Participants

6

Reactant 3

HCID 962WaterHCID 136354590HCID 136354590, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21521295HCID 21521295, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

One introduces into a stainless steel autoclave 15.75 g of N,N-dimethyl-1,2,3,4-tetrahydro-5-phenylazo-7-propyl-8-hydroxyquinolinium bromide (i.e. 0.05 mole) with 170 ml of water and 17 ml of methanol, and one adds 3 g of 5% palladium on charcoal. One hydrogenates under a 3 kg/cm2 to 5 kg/cm2 hydrogen pressure. After cooling, one filters off the catalyst, evaporates the filtrate, and redissolves the residue in ether so as to remove the aniline. One recrystallizes in acetonitrile and one washes again with ether.

Workup

  1. temperatureAfter cooling
  2. customone filters off the catalyst, evaporates the filtrate
  3. dissolutionredissolves the residue in ether so as
  4. customto remove the aniline
  5. customOne recrystallizes in acetonitrile

Sources & evidence

ORD record
ord-f18fa9c0180c40eea0913e305de73d6b
Source dataset
uspto-grants-1976_07
Patent number
US03970454

Reaction notes

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