Acetyl chloride → HCID 11427507, compound

HRID 2382260Notes

Reaction equation

HRID 2382260 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].C(OC(=O)C)(=O)C.[C:12]([O:16][C:17]([NH:19][C:20]1[CH:21]=[C:22]2[C:27](=[CH:28][CH:29]=1)[NH:26][C:25]([CH3:31])([CH3:30])[CH:24]=[C:23]2[CH3:32])=[O:18])([CH3:15])([CH3:14])[CH3:13]>N1C=CC=CC=1.ClCCl>[C:1]([N:26]1[C:27]2[C:22](=[CH:21][C:20]([NH:19][C:17]([O:16][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:18])=[CH:29][CH:28]=2)[C:23]([CH3:32])=[CH:24][C:25]1([CH3:31])[CH3:30])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 7918Acetic AnhydrideHCID 11392086HCID 11392086, compound

Product 1

HCID 11427507HCID 11427507, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

Acetyl chloride (11.1 ml) and acetic anhydride (11.1 ml) were added dropwise to a solution of 6-(tert-butoxycarbonyl)amino-1,2-dihydro-2,2,4-trimethylquinoline (8.5 g) in pyridine (22 ml) and dichloromethane (212 ml). After stirring for 18 h, the reaction mixture was washed with 2 M HCl and water. The organic layer was dried (MgSO4); filtered and concentrated in vacuo. The residue was chromatographed on silicagel in heptane/ethyl acetate=8/2 (v/v) as eluent.

Workup

  1. washthe reaction mixture was washed with 2 M HCl and water
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed on silicagel in heptane/ethyl acetate=8/2 (v/v) as eluent

Sources & evidence

ORD record
ord-e502a77aed044a508e2799687d966756
Source dataset
uspto-grants-2012_09
Patent number
US08258293B2

Reaction notes

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