Formaldehyde → (4aR,10aS)-1-Methyl-1,2,3,4,4a,5,10,10a-octahydrobenzo[g]quinolin-7-ol

HRID 1283989Notes

Reaction equation

HRID 1283989 reaction equation
[NH:1]1[C@@H:10]2[C@@H:5]([CH2:6][C:7]3[CH:14]=[C:13]([OH:15])[CH:12]=[CH:11][C:8]=3[CH2:9]2)[CH2:4][CH2:3][CH2:2]1.[CH2:16]=O.[H][H]>[Pd].C(O)C>[CH3:16][N:1]1[C@@H:10]2[C@@H:5]([CH2:6][C:7]3[CH:14]=[C:13]([OH:15])[CH:12]=[CH:11][C:8]=3[CH2:9]2)[CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 71364636(4aR,10aS)-1,2,3,4,4a,5,10,10a-Octahydrobenzo[g]quinolin-7-olHCID 178418361HCID 178418361, compound

Product 1

HCID 71364635(4aR,10aS)-1-Methyl-1,2,3,4,4a,5,10,10a-octahydrobenzo[g]quinolin-7-ol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 13.3 g. of cis-1,2,3,4,4a,5,10,10a-octahydrobenzo[g]quinolin-7-ol, 5.4 ml. of 35% aqueous formaldehyde solution, and 6 g. of palladium-on-carbon catalyst was diluted to 350 ml. total volume with ethyl alcohol and the mixture was shaken under 400 lbs./sq. in. of hydrogen until uptake ceased. Filtration to remove the catalyst, evaporation of the solvent and crystallization of the resulting residue from ethyl alcohol gave 10.8 g. of solid which on recrystallization from ethyl alcohol yielded cis-1,2,3,4,4a,5,10,10a-octahydro-1-methyl-benzo[g]quinolin-7-ol as a white solid, m.p. 213°-216°C.

Workup

  1. additionA mixture of 13.3 g
  2. filtrationFiltration
  3. customto remove
  4. customthe catalyst, evaporation of the solvent and crystallization of the resulting residue from ethyl alcohol
  5. customgave 10.8 g
  6. customof solid which on recrystallization from ethyl alcohol

Sources & evidence

ORD record
ord-57c4925b9f234ec98fcfd5d82ac6ee70
Source dataset
uspto-grants-1976_08
Patent number
US03976653

Reaction notes

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