Butyryl chloride → HCID 66992376, compound

HRID 557541Notes

Reaction equation

HRID 557541 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 μl) 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-2e4b8a13d4d74953bd0217d85265e85a
Source dataset
uspto-grants-2011_11
Patent number
US08058441B2

Reaction notes

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