p-Anisoyl chloride → HCID 66850584, compound

HRID 655716Notes

Reaction equation

HRID 655716 reaction equation
[NH2:1][C:2]1[C:11]([C:12]#[N:13])=[C:10]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([N+:22]([O-:24])=[O:23])[CH:8]=2)[N:3]=1.[CH3:25][O:26][C:27]1[CH:35]=[CH:34][C:30]([C:31](Cl)=[O:32])=[CH:29][CH:28]=1>N1C=CC=CC=1>[CH3:25][O:26][C:27]1[CH:35]=[CH:34][C:30]([C:31]([N:1]([C:31](=[O:32])[C:30]2[CH:34]=[CH:35][C:27]([O:26][CH3:25])=[CH:28][CH:29]=2)[C:2]2[C:11]([C:12]#[N:13])=[C:10]([NH:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:9]3[C:4](=[CH:5][CH:6]=[C:7]([N+:22]([O-:24])=[O:23])[CH:8]=3)[N:3]=2)=[O:32])=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 7477p-Anisoyl chlorideHCID 668504812-Amino-3-cyano-4-benzylamino-6-nitroquinoline

Product 1

HCID 66850584HCID 66850584, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A suspension of 3.5 g of 2-amino-3-cyano-4-benzylamino-6-nitroquinoline in 50 mL of dry pyridine was refluxed with 5.6 g of 4-methoxybenzoyl chloride for 3.5 hours. The solvent was evaporated in reduced pressure and the residue was suspended in 30 mL of a saturated solution of Na2CO3 in water. The suspension was extracted with 3×25 mL of CH2Cl2. The combined organic extract was evaporated to dryness, the residue was dissolved in diethyl ether and the solution was kept in a refrigerator for a night. The precipitate was filtered off, washed with diethyl ether to give 6.25 g of the title compound, m.p.: 145-148° C. LC-MS: MH+ 588; Ret. time: 7.00 min.

Workup

  1. customThe solvent was evaporated in reduced pressure
  2. extractionThe suspension was extracted with 3×25 mL of CH2Cl2
  3. extractionThe combined organic extract
  4. customwas evaporated to dryness
  5. dissolutionthe residue was dissolved in diethyl ether
  6. waitthe solution was kept in a refrigerator for a night
  7. filtrationThe precipitate was filtered off
  8. washwashed with diethyl ether

Sources & evidence

ORD record
ord-f28251d27f5b4b9a8ee9330e06de591e
Source dataset
uspto-grants-2011_12
Patent number
US08071601B2

Reaction notes

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