Methanol → HCID 12393747, compound

HRID 259019Notes

Reaction equation

HRID 259019 reaction equation
CO.[ClH:3].[NH2:4][C@@H:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:17]CC3C=CC=CC=3)[C:11]=2[C:15]#[N:16])[C@H:6]1[OH:25]>[H][H].[Pd]>[ClH:3].[NH2:4][C@@H:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([OH:17])[C:11]=2[C:15]#[N:16])[C@H:6]1[OH:25]

Participants

5

Reactant 2

HCID 887MethanolHCID 12393669HCID 12393669, compound

Product 1

HCID 12393747HCID 12393747, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 178418361HCID 178418361, compoundSolvent

Procedure

In 20 ml. of methanol is dissolved 200 mg. of trans-2-amino-6-benzyloxy-5-cyano-1-hydroxy-1,2,3,4-tetrahydronaphthalene hydrochloride, followed by the addition of 30 mg. of 5% palladium-on-carbon. The mixture is agitated in hydrogen streams at room temperature for 30 minutes. The catalyst is filtered off and the filtrate is concentrated under reduced pressure. The residue is recrystallized from methanol-ethyl acetate. The procedure yields white crystals of trans-2-amino-5-cyano-1,6-dihydroxy-1,2,3,4-tetrahydronaphthalene hydrochloride. Yield 136 mg.; melting point: 259°-261° C(decomp.).

Workup

  1. filtrationThe catalyst is filtered off
  2. concentrationthe filtrate is concentrated under reduced pressure
  3. customThe residue is recrystallized from methanol-ethyl acetate

Sources & evidence

ORD record
ord-60290aace0f249cbbc6c6dd91417f225
Source dataset
uspto-grants-1977_07
Patent number
US04035512

Reaction notes

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