Dichloromethane → N-(1,3,4,9-tetrahydro-7-hydroxy-2H-carbazol-2-yl)acetamide

HRID 126891

Reaction equation

HRID 126891 reaction equation
C[O:2][C:3]1[CH:15]=[C:14]2[C:6]([C:7]3[CH2:8][CH2:9][CH:10]([NH:16][C:17](=[O:19])[CH3:18])[CH2:11][C:12]=3[NH:13]2)=[CH:5][CH:4]=1.C(Cl)Cl.B(Br)(Br)Br>CO>[OH:2][C:3]1[CH:15]=[C:14]2[C:6]([C:7]3[CH2:8][CH2:9][CH:10]([NH:16][C:17](=[O:19])[CH3:18])[CH2:11][C:12]=3[NH:13]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 25134Boron tribromideHCID 20529238N-(1,3,4,9-tetrahydro-7-methoxy-2H-carbazol-2-yl)acetamide

Product 1

HCID 20529233N-(1,3,4,9-tetrahydro-7-hydroxy-2H-carbazol-2-yl)acetamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
-40 °C

Procedure

A solution of 25.8 g (0.1 mol) of N-(1,3,4,9-tetrahydro-7-methoxy-2H-carbazol-2-yl)acetamide in 2 l. of CH2Cl2 was stirred at -50° to -60° C. under N2 while adding 101 g (0.4 mol) of BBr3 dropwise during 15-30 min. Stirring was continued for 30 min at -55° C. and then 3 hr at room temperature. After cooling to -40° C., 600 ml of MeOH was cautiously added dropwise during 45 min. The reaction mixture was allowed to warm to room temperature (ca. 1 hr) and then evaporated. The residue was dissolved in one l. of 1 N KOH, filtered from insolubles, and the cold filtrate was acidified (pH 3) with conc. HCl. The precipitate was filtered, washed with H2O, and recrystallized from i-PrOH to give the title compound, mp 245°-246°.

Workup

  1. custom3 hr
  2. customat room temperature
  3. temperatureto warm to room temperature (ca. 1 hr)
  4. customevaporated
  5. dissolutionThe residue was dissolved in one l
  6. filtrationof 1 N KOH, filtered from insolubles
  7. filtrationThe precipitate was filtered
  8. washwashed with H2O
  9. customrecrystallized from i-PrOH

Sources & evidence

ORD record
ord-a9fd526ba1d94dfabd0d512a6ea63438
Source dataset
uspto-grants-1981_03
Patent number
US04254134

Linked notes

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