Ammonium Hydroxide → 1H-Inden-1-one, 3-amino-5-hydroxy-2-(4-hydroxyphenyl)-

HRID 1071219Notes

Reaction equation

HRID 1071219 reaction equation
B(Br)(Br)Br.[NH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15]C)[CH:13]=2)[C:8](=[O:17])[C:7]=1[C:18]1[CH:23]=[CH:22][C:21]([O:24]C)=[CH:20][CH:19]=1.[OH-].[NH4+]>ClCCl>[NH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([OH:15])[CH:13]=2)[C:8](=[O:17])[C:7]=1[C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 25134Boron tribromideHCID 389548NSC685853

Product 1

HCID 102860111H-Inden-1-one, 3-amino-5-hydroxy-2-(4-hydroxyphenyl)-Yield 56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boron tribromide (0.5 mL, 5.3 mmol) was added dropwise into a cold (−78° C.) mixture of 3-Amino-5-methoxy-2-(4-methoxyphenyl)-1H-inden-1-one (250 mg, 0.89 mmol), and dichloromethane (2.0 mL). The reaction mixture was allowed to come gradually to room temperature and stirred for 1 hour. The mixture was poured onto ice containing ammonium hydroxide (1 mL) and extracted with ethyl acetate. The organic extracts were washed with brine and were dried over MgSO4. Evaporation and flash chromatography (5%-10% ETOH/dichloromethane) gave (126 mg, 56% yield) of the product as a purple solid: mp 260-265° C.;

Workup

  1. customto come gradually to room temperature
  2. additionThe mixture was poured onto ice
  3. extractionextracted with ethyl acetate
  4. washThe organic extracts were washed with brine
  5. dry with materialwere dried over MgSO4
  6. customEvaporation and flash chromatography (5%-10% ETOH/dichloromethane)

Sources & evidence

ORD record
ord-4640fb60f3bc46a5b3b0977672af7e52
Source dataset
uspto-grants-2005_06
Patent number
US06903238B2

Reaction notes

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