Methanol → HCID 12393752, compound

HRID 259021Notes

Reaction equation

HRID 259021 reaction equation
CO.[ClH:3].C([O:11][C:12]1[C:13]([C:32]#[N:33])=[C:14]2[C:19](=[CH:20][CH:21]=1)[C@@H:18]([OH:22])[C@@H:17]([N:23](CC1C=CC=CC=1)[CH3:24])[CH2:16][CH2:15]2)C1C=CC=CC=1>[H][H].[Pd]>[ClH:3].[C:32]([C:13]1[C:12]([OH:11])=[CH:21][CH:20]=[C:19]2[C:14]=1[CH2:15][CH2:16][C@H:17]([NH:23][CH3:24])[C@@H:18]2[OH:22])#[N:33]

Participants

5

Reactant 2

HCID 887MethanolHCID 68119420HCID 68119420, compound

Product 1

HCID 12393752HCID 12393752, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 178418361HCID 178418361, compoundSolvent

Procedure

In 30 ml. of methanol are suspended 250 mg. of cis-6-benzyloxy-2-(N-benzyl-N-methylamino)-5-cyano-1-hydroxy-1,2,3,4-tetrahydronaphthalene hydrochloride and 5 % palladium-on-carbon, and the mixture is agitated in hydrogen streams at room temperature for 30 minutes. After the reaction, the catalyst is filtered off and the filtrate is concentrated under reduced pressure. The procedure provides cis-5-cyano-1,6-dihydroxy-2-methylamino-1,2,3,4-tetrahydronaphthalene hydrochloride as a white precipitate. Recrystallization from ethanol-ethyl acetate provides colorless crystals melting at 226°-227° C(decomp.). Yield 112 mg.

Workup

  1. customAfter the reaction
  2. filtrationthe catalyst is filtered off
  3. concentrationthe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-61cf53d96a88491d90a24642f5ced267
Source dataset
uspto-grants-1977_07
Patent number
US04035512

Reaction notes

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