Methane → HCID 21399002, compound

HRID 1439262Notes

Reaction equation

HRID 1439262 reaction equation
[BrH:1].C([NH:9][CH:10]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[C:16]([OH:21])[CH:15]=1)[CH2:11][OH:12])C1C=CC=CC=1.C>CO>[BrH:1].[NH2:9][CH:10]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[C:16]([OH:21])[CH:15]=1)[CH2:11][OH:12]

Participants

4

Reactant 2

HCID 297MethaneHCID 21398964HCID 21398964, compound

Product 1

HCID 21399002HCID 21399002, compoundYield 81.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

21.5 gm (61 millimols) of 2-benzylamino-3-(3'-hydroxy-4'-methyl-phenyl)-1-propanol hydrobromide (see Example 2) were dissolved in 250 ml of methanol, 6 gm of 5% palladized charcoal were added to the solution, and the mixture was hydrogenated at 60° C and 5 atmospheres pressure. After the debenzylation had gone to completion, the reaction mixture was filtered, the methanol was distilled in vacuo out of the filtrate, the residue was dissolved in hot acetonitrile, and the solution was allowed to cool. The substance which crystallized out was collected by suction filtration and dried, yielding 13 gm (81.5% of theory) of 2-amino-3-(3'-hydroxy-4'-methyl-phenyl)-1-propanol hydrobromide having a melting point of 115°-117° C.

Workup

  1. customwas hydrogenated at 60° C
  2. filtrationthe reaction mixture was filtered
  3. distillationthe methanol was distilled in vacuo out of the filtrate
  4. dissolutionthe residue was dissolved in hot acetonitrile
  5. temperatureto cool
  6. customThe substance which crystallized out
  7. filtrationwas collected by suction filtration
  8. customdried

Sources & evidence

ORD record
ord-0875d10d19dd49989a8c5e6fc05c4331
Source dataset
uspto-grants-1977_11
Patent number
US04058642

Reaction notes

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