Stannous chloride dihydrate → HCID 86641449, compound

HRID 1189943Notes

Reaction equation

HRID 1189943 reaction equation
O.O.[Sn](Cl)Cl.[F:6][C:7]([F:24])([F:23])[C:8]([NH:10][CH2:11][C:12]#[C:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-])=O)[CH:15]=1)=[O:9]>C(O)C>[NH2:20][C:16]1[CH:15]=[C:14]([C:13]#[C:12][CH2:11][NH:10][C:8](=[O:9])[C:7]([F:6])([F:23])[F:24])[CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 86641448HCID 86641448, compound

Product 1

HCID 86641449HCID 86641449, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Tin(II) chloride dihydrate was added (6.5 g, 28.67 mmol) to a solution of 2,2,2-trifluoro-N-(3-(3-nitrophenyl)prop-2-ynyl)acetamide (1.95 g, 7.16 mmol) in ethanol and the reaction mixture was stirred under reflux overnight. The mixture was concentrated under reduced pressure to give dark brown viscous liquid which was partitioned between saturated aqueous NaHCO3 and EtOAc. Organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give N-(3-(3-aminophenyl)prop-2-ynyl)-2,2,2-trifluoroacetamide as brown oil. Yield (0.75 g, 43%); 1H NMR (400 MHz, DMSO-d6) δ 7.28 (s, 1H), 6.94 (t, J=7.8 Hz, 1H), 6.44-6.37 (m, 3H), 5.09 (bs, 2H), 3.99 (s, 2H).

Workup

  1. temperatureunder reflux overnight
  2. concentrationThe mixture was concentrated under reduced pressure
  3. customto give dark brown viscous liquid which
  4. customwas partitioned between saturated aqueous NaHCO3 and EtOAc
  5. dry with materialOrganic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a512f941e39c48ad90eac43798c66ef5
Source dataset
uspto-grants-2014_03
Patent number
US08674137B2

Reaction notes

Loading…