Formaldehyde → HCID 68132380, compound

HRID 268301Notes

Reaction equation

HRID 268301 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([CH:10]2[C:19]3[C:14](=[CH:15][C:16]([OH:22])=[C:17]([O:20][CH3:21])[CH:18]=3)[CH2:13][NH:12][CH2:11]2)[CH:6]=[CH:7][C:8]=1[Cl:9].[CH2:23]=O>[Ni].CO>[ClH:2].[Cl:2][C:3]1[CH:4]=[C:5]([CH:10]2[C:19]3[C:14](=[CH:15][C:16]([OH:22])=[C:17]([O:20][CH3:21])[CH:18]=3)[CH2:13][N:12]([CH3:23])[CH2:11]2)[CH:6]=[CH:7][C:8]=1[Cl:9]

Participants

5

Reactant 2

HCID 712FormaldehydeHCID 68131881HCID 68131881, compound

Product 1

HCID 68132380HCID 68132380, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

The free base prepared from 3.7 g. of rac.-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-6-methoxy-7-isoquinolinol hydrochloride is treated with 100 ml. of methanol and 5 ml. of 35% formaldehyde solution and, after standing at room temperature for 2 hours, hydrogenated with 5 g. of Raney nickel. After filtration, evaporation and acidification with ethanolic hydrogen chloride, a crystallized product is obtained. Recrystallization from methanol-ether gives rac.-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-6-methoxy-2-methyl-7-isoquinolinol hydrochloride, m.p. 253°-254°C.

Workup

  1. customThe free base prepared from 3.7 g
  2. filtrationAfter filtration, evaporation and acidification with ethanolic hydrogen chloride
  3. customa crystallized product is obtained
  4. customRecrystallization from methanol-ether

Sources & evidence

ORD record
ord-29f6e5b24da6475186ec5245a8112b75
Source dataset
uspto-grants-1976_03
Patent number
US03947456

Reaction notes

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