Triethylamine → HCID 19592677, compound

HRID 613478Notes

Reaction equation

HRID 613478 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[C:7]2[O:12][C:13](=[O:22])[C:14]1[C:19]([Cl:20])=[CH:18][CH:17]=[CH:16][C:15]=1[Cl:21].[Cl:23][C:24]1[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[C:25]=1[C:26](Cl)=[O:27].C(N(CC)CC)C>C(Cl)CCl.ClCCl>[Cl:21][C:15]1[CH:16]=[CH:17][CH:18]=[C:19]([Cl:20])[C:14]=1[C:13]([O:12][C:7]1[C:6]2[C:11](=[C:2]([NH:1][C:26](=[O:27])[C:25]3[C:24]([Cl:23])=[CH:32][CH:31]=[CH:30][C:29]=3[Cl:33])[CH:3]=[CH:4][CH:5]=2)[N:10]=[CH:9][CH:8]=1)=[O:22]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 783922,6-Dichlorobenzoyl chlorideHCID 195924468-Amino-4-quinolinyl 2,6-dichlorobenzoate

Product 1

HCID 19592677HCID 19592677, compoundYield 90.9%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 8-amino-4-(2,6-dichlorobenzoyloxy)quinoline (210 mg), 2,6-dichlorobenzoyl chloride (145 mg) and triethylamine (191 mg) in ethylene chloride (3 ml) was stirred for 24 hours at 70° C. The mixture was diluted with dichloromethane, washed with water, dried over magnesium sulfate and evaporated in vacuo. The residue was washed with diethyl ether to give 4-(2,6-dichlorobenzoyloxy)-8-(2,6-dichlorobenzoylamino)quinoline (290 mg).

Workup

  1. washwashed with water
  2. dry with materialdried over magnesium sulfate
  3. customevaporated in vacuo
  4. washThe residue was washed with diethyl ether

Sources & evidence

ORD record
ord-91068dc9675f42c8bed51b89d9363791
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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