Triethylamine → HCID 67041312, compound

HRID 606137Notes

Reaction equation

HRID 606137 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[C:15]1([C:21]2[O:25][N:24]=[C:23]([CH2:26][NH2:27])[CH:22]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(N(CC)CC)C>ClCCl>[N+:12]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:2]=1[NH:27][CH2:26][C:23]1[CH:22]=[C:21]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[O:25][N:24]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2)([O-:14])=[O:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 5200315(5-phenylisoxazol-3-yl)methylamineHCID 112758084-Chloro-3-nitroquinoline

Product 1

HCID 67041312HCID 67041312, compoundYield 76.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of 4-chloro-3-nitroquinoline (2.29 g, 11.0 mmol) and (5-phenylisoxazol-3-yl)methylamine (1.92 g, 11.0 mmol) in dichloromethane (200 mL) was cooled to 0° C., and triethylamine (2.30 mL, 16.5 mmol) was added. The resultant solution was allowed to warm to room temperature slowly and stirred overnight. The volatiles were removed under reduced pressure, and the residue was purified by flash column chromatography on silica gel (eluting with 3% to 8% methanol in dichloromethane) to provide 2.90 g of 3-nitro-N-[(5-phenylisoxazol-3-yl)methyl]quinolin-4-amine.

Workup

  1. temperatureto warm to room temperature slowly
  2. customThe volatiles were removed under reduced pressure
  3. customthe residue was purified by flash column chromatography on silica gel (eluting with 3% to 8% methanol in dichloromethane)

Sources & evidence

ORD record
ord-728419928fa9413e9b5bf49fe8f50974
Source dataset
uspto-grants-2011_03
Patent number
US07915281B2

Reaction notes

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