Water → (7-benzyloxy-3-nitroquinolin-4-yl)(tetrahydro-2H-pyran-4-ylmethyl)amine

HRID 2426358Notes

Reaction equation

HRID 2426358 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([CH2:7][NH2:8])[CH2:3][CH2:2]1.[CH2:9]([O:16][C:17]1[CH:26]=[C:25]2[C:20]([C:21](Cl)=[C:22]([N+:27]([O-:29])=[O:28])[CH:23]=[N:24]2)=[CH:19][CH:18]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(N(CC)CC)C.O>CN(C)C=O>[CH2:9]([O:16][C:17]1[CH:26]=[C:25]2[C:20]([C:21]([NH:8][CH2:7][CH:4]3[CH2:5][CH2:6][O:1][CH2:2][CH2:3]3)=[C:22]([N+:27]([O-:29])=[O:28])[CH:23]=[N:24]2)=[CH:19][CH:18]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 27732104-Aminomethyltetrahydropyran2×HCID 210757517-(Benzyloxy)-4-chloro-3-nitroquinoline

Product 1

HCID 67051153(7-benzyloxy-3-nitroquinolin-4-yl)(tetrahydro-2H-pyran-4-ylmethyl)amineYield 85.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-tetrahydro-2H-pyran-4-ylmethanamine (40 g, 0.347 mol) was added to a stirred solution of 7-(benzyloxy)-4-chloro-3-nitroquinoline (55 g, 0.176 mol) and triethylamine (50.96 g, 0.503 mol) in N,N-dimethylformamide (DMF) (250 mL) at 0° C. After complete addition, the ice bath was removed. To consume the remaining starting material, additional (1-tetrahydro-2H-pyran-4-ylmethanamine (11 g, 95.50 mmol) was added. The reaction proceeded at ambient temp for 3 days, then was chilled in an ice-water bath. Water (250 mL) was added drop wise which caused a solid to precipitate out of solution. After stirring for 1 hour, the solid was collected by filtration, washed with diethyl ether (800 mL), and dried under reduced pressure to afford 7-(benzyloxy)-3-nitro-N-(tetrahydro-2H-pyran-4-ylmethyl)quinolin-4-amine (59.3 g) as a bright yellow solid.

Workup

  1. additionAfter complete addition
  2. customthe ice bath was removed
  3. customTo consume the
  4. temperaturewas chilled in an ice-water bath
  5. customto precipitate out of solution
  6. filtrationthe solid was collected by filtration
  7. washwashed with diethyl ether (800 mL)
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-9398847a721545b7be2ce11e5256f5f5
Source dataset
uspto-grants-2011_06
Patent number
US07968563B2

Reaction notes

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