Pyridine → HCID 19593010, compound

HRID 613554Notes

Reaction equation

HRID 613554 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]=[CH:14][C:13]([CH2:17][OH:18])=[C:12]2[N:19]1[CH:23]=[CH:22][N:21]=[CH:20]1)=[O:5].N1C=CC=CC=1.[C:35](OC(=O)C)(=[O:37])[CH3:36]>ClCCl>[C:35]([O:18][CH2:17][C:13]1[CH:14]=[N:15][C:16]2[C:11]([C:12]=1[N:19]1[CH:23]=[CH:22][N:21]=[CH:20]1)=[CH:10][CH:9]=[CH:8][C:7]=2[NH:6][C:4](=[O:5])[C:3]1[C:24]([Cl:28])=[CH:25][CH:26]=[CH:27][C:2]=1[Cl:1])(=[O:37])[CH3:36]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 19592507HCID 19592507, compound

Product 1

HCID 19593010HCID 19593010, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 8-(2,6-dichlorobenzoylamino)-3-hydroxymethyl-4-(imidazol-1-yl)quinoline (250 mg) in dichloromethane (3 ml) were dropwise added pyridine (57.4 mg) and acetic anhydride (0.12 ml) at ambient temperature, and the mixture was stirred for 22 hours at ambient temperature. The mixture was concentrated in vacuo, and the residue was dissolved in ethyl acetate. The mixture was washed with water, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by flash chromatography on silica gel (methanol-dichloromethane) to give 3-acetoxymethyl-8-(2,6-dichlorobenzoylamino)-4-(imidazol-1-yl)quinoline (270 mg).

Workup

  1. customat ambient temperature
  2. concentrationThe mixture was concentrated in vacuo
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washThe mixture was washed with water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by flash chromatography on silica gel (methanol-dichloromethane)

Sources & evidence

ORD record
ord-e763fe81ca314bc7893710180664c329
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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