Butyryl chloride → HCID 66992376, compound

HRID 2382261Notes

Reaction equation

HRID 2382261 reaction equation
[C:1](Cl)(=[O:5])[CH2:2][CH2:3][CH3:4].[C:7]([O:11][C:12]([NH:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[NH:21][C:20]([CH3:26])([CH3:25])[CH:19]=[C:18]2[CH3:27])=[O:13])([CH3:10])([CH3:9])[CH3:8]>N1C=CC=CC=1>[C:7]([O:11][C:12]([NH:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[N:21]([C:1](=[O:5])[CH2:2][CH2:3][CH3:4])[C:20]([CH3:26])([CH3:25])[CH:19]=[C:18]2[CH3:27])=[O:13])([CH3:10])([CH3:8])[CH3:9]

Participants

4

Reactant 2

HCID 8855Butyryl chlorideHCID 11392086HCID 11392086, compound

Product 1

HCID 66992376HCID 66992376, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Butyryl chloride (185 l) was added dropwise to a solution of 6-(tert-butoxycarbonyl)amino-1,2-dihydro-2,2,4-trimethylquinoline (50 mg) and a catalytic amount of N,N-dimethylaminopyridine in pyridine (4 ml). After stirring for 18 h, the reaction mixture was concentrated in vacuo. The residue was dissolved in ethyl acetate and washed with water. The organic layer was separated, dried (MgSO4) and concentrated in vacuo. The residue was chromatographed on silicagel in heptane/ethyl acetate=1/0=>7/3 (v/v) as eluent.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with water
  4. customThe organic layer was separated
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue was chromatographed on silicagel in heptane/ethyl acetate=1/0=>7/3 (v/v) as eluent

Sources & evidence

ORD record
ord-942e8210afbf42668387d6d999a3f5ff
Source dataset
uspto-grants-2012_09
Patent number
US08258293B2

Reaction notes

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