Water → 4-(3-Amino-6-benzyloxy-7-methoxyquinolin-4-ylamino)-3-fluorobenzonitrile

HRID 1467380Notes

Reaction equation

HRID 1467380 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][C:18]=1[O:19][CH3:20])[N:15]=[CH:14][C:13]([N+:21]([O-])=O)=[C:12]2[NH:24][C:25]1[CH:32]=[CH:31][C:28]([C:29]#[N:30])=[CH:27][C:26]=1[F:33])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.O.[Sn](Cl)Cl.O.C(OCC)(=O)C>C(O)C>[NH2:21][C:13]1[CH:14]=[N:15][C:16]2[C:11]([C:12]=1[NH:24][C:25]1[CH:32]=[CH:31][C:28]([C:29]#[N:30])=[CH:27][C:26]=1[F:33])=[CH:10][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[C:18]([O:19][CH3:20])[CH:17]=2

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 61436Stannous chloride dihydrateHCID 666119184-(6-Benzyloxy-7-methoxy-3-nitroquinolin-4-ylamino)-3-fluorobenzonitrile

Product 1

HCID 666118064-(3-Amino-6-benzyloxy-7-methoxyquinolin-4-ylamino)-3-fluorobenzonitrileYield 56.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

4-(6-Benzyloxy-7-methoxy-3-nitroquinolin-4-ylamino)-3-fluorobenzonitrile (6.50 g, 14.62 mmol) and tin(II) chloride dihydrate (14.70 g, 65.15 mmol) were dissolved in ethanol (780 ml). The reaction solution was subsequently stirred at 70° C. for 30 min. When the reaction was complete (TLC, LC-MS), water (2 l) and ethyl acetate (1.5 l) was added, and the mixture was stirred vigorously for a further 30 min. The suspension obtained was filtered through kieselguhr. The aqueous phase was extracted again with ethyl acetate (1 l), and the combined organic phases were washed with water (500 ml). After the organic phase had been dried over Na2SO4, the solid material was filtered off with suction, and the filtrate was evaporated to dryness in vacuo, giving 4-(3-amino-6-benzyloxy-7-methoxyquinolin-4-ylamino)-3-fluorobenzonitrile (3.40 g, 8.2 mmol) as solid. MS: 415.1 (M+H+), TLC (HPTLC): Rf=0.47 (ethyl acetate).

Workup

  1. additionwas added
  2. stirringthe mixture was stirred vigorously for a further 30 min
  3. customThe suspension obtained
  4. filtrationwas filtered through kieselguhr
  5. extractionThe aqueous phase was extracted again with ethyl acetate (1 l)
  6. washthe combined organic phases were washed with water (500 ml)
  7. dry with materialAfter the organic phase had been dried over Na2SO4
  8. filtrationthe solid material was filtered off with suction
  9. customthe filtrate was evaporated to dryness in vacuo

Sources & evidence

ORD record
ord-02970c6ed1d443689547c7fb861f9d93
Source dataset
uspto-grants-2015_04
Patent number
US09000153B2

Reaction notes

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