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

HRID 1607917Notes

Reaction equation

HRID 1607917 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 withether, 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 withether, and
  4. dissolutionredissolved in 1N
  5. customthe resultant precipitate is collected as crude product
  6. customRecrystallization from H2O

Sources & evidence

ORD record
ord-9b81a0f79eac4448a16700c97ae663a9
Source dataset
uspto-grants-1989_09
Patent number
US04868199

Reaction notes

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