HCID 86664381, compound → HCID 86664382, compound

HRID 1019998Notes

Reaction equation

HRID 1019998 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:17]=[C:16]([N+:18]([O-])=O)[CH:15]=[C:14]2[C:9]=1[CH2:10][CH2:11][N:12]([C:21](=[O:26])[C:22]([F:25])([F:24])[F:23])[CH2:13]2>CO>[NH2:18][C:16]1[CH:15]=[C:14]2[C:9]([CH2:10][CH2:11][N:12]([C:21](=[O:26])[C:22]([F:25])([F:23])[F:24])[CH2:13]2)=[C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])[CH:17]=1

Participants

3

Reactant 1

HCID 86664381HCID 86664381, compound

Product 1

HCID 86664382HCID 86664382, compoundYield 71.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

1-[5-(2-Chloro-phenyl)-7-nitro-3,4-dihydro-1H-isoquinolin-2-yl]-2,2,2-trifluoro-ethanone (760 mg, 1.97 mmoles) was dissolved in methanol (10 mls) and stannous chloride dihydrate (2.23 g, 9.87 mmoles) was added. The yellow coloured reaction mixture was heated to 65° C. for 2 hours, evaporated and partitioned between ethylacetate (50 mls) and water (50 mls). The solution was then basified by the addition of potassium hydroxide solution (10%) to a pH 11-12. The whole mixture was then filtered through a Celite pad and washed with ethylacetate (20 mls), water (20 mls) and brine (40 mls) and finally dried over anhydrous magnesium sulphate. After filtration and evaporation the yellow oil was triturated with ether (2×25 mls) and hexane (25 mls) to give an oily solid (500 mg, 60% yield). LC-MS (retention 3.60, M+H 356).

Workup

  1. customreaction mixture
  2. customevaporated
  3. custompartitioned between ethylacetate (50 mls) and water (50 mls)
  4. additionThe solution was then basified by the addition of potassium hydroxide solution (10%) to a pH 11-12
  5. filtrationThe whole mixture was then filtered through a Celite pad
  6. washwashed with ethylacetate (20 mls), water (20 mls) and brine (40 mls)
  7. dry with materialfinally dried over anhydrous magnesium sulphate
  8. filtrationAfter filtration and evaporation the yellow oil
  9. customwas triturated with ether (2×25 mls) and hexane (25 mls)

Sources & evidence

ORD record
ord-989d4a94a9ff4764b0e28260ed2a3256
Source dataset
uspto-grants-2014_05
Patent number
US08716302B2

Reaction notes

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