Methanol → HCID 21521293, compound

HRID 918215Notes

Reaction equation

HRID 918215 reaction equation
[Br-:1].[CH3:2][N+:3]1([CH3:22])[C:12]2[C:7](=[C:8]([N:14]=NC3C=CC=CC=3)[CH:9]=[CH:10][C:11]=2[OH:13])[CH2:6][CH2:5][CH2:4]1.CO.[H][H]>[Pd].O>[Br-:1].[CH3:2][N+:3]1([CH3:22])[C:12]2[C:7](=[C:8]([NH2:14])[CH:9]=[CH:10][C:11]=2[OH:13])[CH2:6][CH2:5][CH2:4]1

Participants

6

Reactant 3

HCID 887MethanolHCID 136354588HCID 136354588, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21521293HCID 21521293, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

Into a stainless steel autoclave, one introduces 36.2 g of N,N-dimethyl-1,2,3,4-tetrahydro-5-phenylazo-8-hydroxyquinolinium bromide (i.e. 0.1 mole), 200 ml of methanol and 3 g of 5% palladium on charcoal. The reduction is carried out at a pressure of 3-5 kg/cm2 of hydrogen and a temperature of 50°-60°C. After cooling, one adds a sufficient quantity of water to dissolve the entire mass, then one filters off the catalyst. One evaporates the filtrate to the dry state. The residue is extracted by means of ether so as to remove the aniline. One washes, with acetone, the clear brown compound that is obtained.

Workup

  1. customa temperature of 50°-60°C
  2. temperatureAfter cooling
  3. dissolutionto dissolve the entire mass
  4. customOne evaporates the filtrate to the dry state
  5. extractionThe residue is extracted by means of ether so as
  6. customto remove the aniline
  7. customOne washes, with acetone, the clear brown compound that is obtained

Sources & evidence

ORD record
ord-eae15c7f971b45cc9d743504a091be6d
Source dataset
uspto-grants-1976_07
Patent number
US03970454

Reaction notes

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