HCID 22466695, compound → HCID 22466599, compound

HRID 612245Notes

Reaction equation

HRID 612245 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:22][CH3:23])=[C:16]([N+:19]([O-])=O)[CH:17]=3)[N:12]=[CH:11][C:10]=2[C:24]#[N:25])=[C:4]([F:26])[CH:3]=1.O.O.[Sn](Cl)(Cl)(Cl)Cl>C(O)C>[NH2:19][C:16]1[CH:17]=[C:18]2[C:13](=[CH:14][C:15]=1[O:22][CH3:23])[N:12]=[CH:11][C:10]([C:24]#[N:25])=[C:9]2[NH:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=1[F:26]

Participants

4

Reactant 2

HCID 22466695HCID 22466695, compoundHCID 85782573Tin tetrachloride dihydrate

Product 1

HCID 22466599HCID 22466599, compoundYield 76.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 500 mg (1.34 mmol) 4-[(4-chloro-2-fluorophenyl)amino]-7-methoxy-6-nitro-3-quinolinecarbonitrile, 20 ml ethanol and 1.52 ml (6.71 mmol) tin chloride dihydrate was heated to reflux under N2. At 3 hours, removed heat, added ice water and made basic with sodium bicarbonate. Stirred for several hours and extracted with chloroform. Dried organic layer with sodium sulfate, stripped solvent and dried in vacuo, giving 350 mg of green solid: mass spectrum (electrospray m/e): M+H=342.9, 344.8.

Workup

  1. temperaturewas heated
  2. temperatureto reflux under N2
  3. customremoved
  4. temperatureheat
  5. additionadded ice water
  6. extractionextracted with chloroform
  7. customdried in vacuo

Sources & evidence

ORD record
ord-d07cd032658949d0826f502bd9b4c41e
Source dataset
uspto-grants-1999_12
Patent number
US06002008

Reaction notes

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