HCID 14793483, compound → HCID 23042321, compound

HRID 2166223Notes

Reaction equation

HRID 2166223 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[C:5]([OH:11])=[C:4]([CH:12]([CH3:14])[CH3:13])[CH:3]=1.[H][H]>CO.[Pd]>[BrH:1].[NH2:8][C:6]1[CH:7]=[CH:2][CH:3]=[C:4]([CH:12]([CH3:13])[CH3:14])[C:5]=1[OH:11]

Participants

5

Reactant 2

HCID 14793483HCID 14793483, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 23042321HCID 23042321, compoundYield 40.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

4-Bromo-2-isopropyl-6-nitrophenol (63.1 g) was dissolved in methanol (442 ml) and to the solution was added 5% Pd-C (11.0 g, water content: 50%). The mixture was subjected to catalytic reduction for 2.5 hours with bubbling hydrogen at hydrogen pressure of 1 to 2 kg/cm2 with maintaining the external temperature at about 25° C. After completion of the reaction, Pd-C was filtered off and the filtrate was concentrated under reduced pressure at an external temperature of not more than 70° C. Then, the residue was washed with ethyl acetate (200 ml) and dried to obtain 2-amino-6-isopropylphenol hydrobromide (23.0 g, 40.8%). The product was recrystallized from methanoldiethyl ether to obtain colorless plates, m.p. 210°-213° C. (decomp.).

Workup

  1. filtrationwas filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure at an external temperature of not more than 70° C
  3. washThen, the residue was washed with ethyl acetate (200 ml)
  4. customdried

Sources & evidence

ORD record
ord-2dfcf7f7943f46478ce273446138765b
Source dataset
uspto-grants-1990_07
Patent number
US04943666

Reaction notes

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