Hydrogen Bromide → 4-[2-(4-Aminophenyl)ethyl]benzene-1,2-diol

HRID 34333Notes

Reaction equation

HRID 34333 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][C:13]2[CH:19]=[CH:18][C:16]([NH2:17])=[CH:15][CH:14]=2)[CH:6]=[CH:7][C:8]=1[O:9]C.Br>>[OH:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][C:13]2[CH:14]=[CH:15][C:16]([NH2:17])=[CH:18][CH:19]=2)[CH:6]=[CH:7][C:8]=1[OH:9]

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 142560244-(3,4-Dimethoxyphenethyl)aniline

Product 1

HCID 142558504-[2-(4-Aminophenyl)ethyl]benzene-1,2-diol

Procedure

A mixture of 20 g (78 mmol) of 4-[2-[3,4-dimethoxyphenyl)ethyl]aniline which is prepared in Preparation 1 above and 300 ml of of 48% hydrobromic acid is stirred at reflux under nitrogen for seven hours and at room temperature overnight. The resultant precipitate is collected, washed with ether, and redissolved in 1N.NaOH. The solution is acidified to pH 6 with glacial HOAc and the resultant precipitate is collected as crude product. Recrystallization from H2O and then from MeOH yields the 4-[2-(3,4-dihydroxyphenyl)ethyl]benzenamine as an acetate salt; yield, 13.4 g (76%), mp 216°-218° C.

Workup

  1. customis prepared in Preparation 1 above
  2. customThe resultant precipitate is collected
  3. washwashed with ether
  4. dissolutionredissolved in 1N
  5. customthe resultant precipitate is collected as crude product
  6. customRecrystallization from H2O

Sources & evidence

ORD record
ord-75658df742024e178d977040072d1b5f
Source dataset
uspto-grants-1988_08
Patent number
US04761424

Reaction notes

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