Water → HCID 86633719, compound

HRID 388597Notes

Reaction equation

HRID 388597 reaction equation
[Cl:1][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[C:10](Cl)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.C(N(CC)CC)C.[O:23]1[CH2:28][CH2:27][CH:26]([CH2:29][NH2:30])[CH2:25][CH2:24]1.O>CN(C=O)C>[Cl:1][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[C:10]([NH:30][CH2:29][CH:26]2[CH2:27][CH2:28][O:23][CH2:24][CH2:25]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 27732104-AminomethyltetrahydropyranHCID 27851382,4-Dichloro-3-nitroquinoline

Product 1

HCID 86633719HCID 86633719, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 2,4-dichloro-3-nitroquinoline (6 g, 25 mmol) in DMF (100 mL) was cooled to 0° C. Triethylamine (10.0 mL, 74.4 mmol) was added, and then tetrahydro-2H-pyran-4-ylmethylamine (see U.S. Patent Application Publication No. 2004/0147543 (Hays et al.) Examples 477-480) (3.4 g, 0.030 mol) was added slowly. Additional DMF was added, and the reaction was stirred at room temperature for one hour and cooled to 0° C. Water (300 mL) was added, and the mixture was maintained at 0° C. for 30 minutes. A precipitate was present and was isolated by filtration and washed sequentially with water and diethyl ether to provide 7 g of 2-chloro-3-nitro-N-(tetrahydro-2H-pyran-4-ylmethyl)quinolin-4-amine as a yellow solid.

Workup

  1. temperaturecooled to 0° C
  2. temperaturethe mixture was maintained at 0° C. for 30 minutes
  3. customwas isolated by filtration
  4. washwashed sequentially with water and diethyl ether

Sources & evidence

ORD record
ord-208b22e08a494b67a80189aed24213dd
Source dataset
uspto-grants-2013_02
Patent number
US08377957B2

Reaction notes

Loading…