Ethanol → Hydrogen Bromide

HRID 905291Notes

Reaction equation

HRID 905291 reaction equation
[BrH:1].C([N:9]([CH2:22][C:23]([C:25]1[CH:30]=[CH:29][C:28]([O:31][C:32](=[O:37])[C:33]([CH3:36])([CH3:35])[CH3:34])=[C:27]([O:38][C:39](=[O:44])[C:40]([CH3:43])([CH3:42])[CH3:41])[CH:26]=1)=[O:24])[CH2:10][CH2:11][NH:12][C:13](=[O:21])[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)C1C=CC=CC=1.C(O)C>O.[C].[Pd]>[C:39]([O:38][C:27]1[CH:26]=[C:25]([CH:23]([OH:24])[CH2:22][NH:9][CH2:10][CH2:11][NH:12][C:13](=[O:21])[CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:30]=[CH:29][C:28]=1[O:31][C:32](=[O:37])[C:33]([CH3:35])([CH3:36])[CH3:34])(=[O:44])[C:40]([CH3:41])([CH3:42])[CH3:43].[BrH:1]

Participants

6

Reactant 2

HCID 702EthanolHCID 20446768HCID 20446768, compound

Product 2

HCID 260Hydrogen BromideYield 561.1%HCID 12876234HCID 12876234, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 962WaterSolvent

Procedure

A solution of 2-{N-benzyl-N-[2-(2-phenylacetamido)ethyl]amino}-3',4'-bis(pivaloyloxy)acetophenone hydrobromide (2.5 g.) in a mixture (50 ml.) containing 70% v/v of ethanol in water was hydrogenated for 18 hours at a pressure of 3.5 kg./cm2 at room temperature using 10% palladium-carbon (0.8 g.). The catalyst was separated by filtration and the filtrate evaporated. Trituration of the residue with ether (30 ml.) containing several drops of ethanol gave 1-[3,4-bis(pivaloyloxy)phenyl]-2-[2-(2-phenylacetamido)ethylamino]ethanol as its hydrobromide (1.7 g.) m.p. 111°-113° C. (hemi-hydrate).

Workup

  1. customat room temperature
  2. customThe catalyst was separated by filtration
  3. customthe filtrate evaporated
  4. additionTrituration of the residue with ether (30 ml.) containing several drops of ethanol

Sources & evidence

ORD record
ord-7c4e016343a84ff5b1b6ad4d4c391707
Source dataset
uspto-grants-1983_12
Patent number
US04423070

Reaction notes

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