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

HRID 1649850Notes

Reaction equation

HRID 1649850 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 1 N.NaOH. The solution is acidified to pH 6 with glacial HOAc and the resultant precipitate is collected as crude product. Recrystallization from H20 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 1 N
  5. customthe resultant precipitate is collected as crude product
  6. customRecrystallization from H20

Sources & evidence

ORD record
ord-dcab8b41bd6a427b8e737271b10cc322
Source dataset
uspto-grants-1990_05
Patent number
US04921871

Reaction notes

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