Chloroacetone → HCID 90046976, compound

HRID 1504996Notes

Reaction equation

HRID 1504996 reaction equation
[C:1]([S:5]([C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][C:17]=1[OH:18])[N:14]=[CH:13][CH:12]=[C:11]2[Cl:19])(=[O:7])=[O:6])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].Cl[CH2:27][C:28](=[O:30])[CH3:29]>CN(C=O)C>[C:1]([S:5]([C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][C:17]=1[O:18][CH2:27][C:28](=[O:30])[CH3:29])[N:14]=[CH:13][CH:12]=[C:11]2[Cl:19])(=[O:6])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 136628985HCID 136628985, compound

Product 1

HCID 90046976HCID 90046976, compoundYield 32.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 6-(tert-butylsulfonyl)-4-chloroquinolin-7-ol (500 mg, 1.668 mmol) in DMF (8162 μl) was added K2CO3 (692 mg, 5.00 mmol) followed by 1-chloropropan-2-one (178 μl, 2.502 mmol). This was heated to 60° C. for 30 min. The crude sample was purified via Biotage normal phase chromatography (25 g SNAP column, 0%-65%, 65%. hex/EtOAc). The pure product containing-fractions were combined and concentrated leading to the product as an off-white solid: 1-((6-(tert-butylsulfonyl)-4-chloroquinolin-7-yl)oxy)propan-2-one (192 mg, 0.540 mmol, 32.3% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.34 (s, 9H) 2.27 (s, 3H) 5.21 (s, 2H) 7.64 (s, 1H) 7.76 (d, J=4.80 Hz, 1H) 8.67 (s, 1H) 8.93 (d, J=4.80 Hz, 1H). MS: m/z: 356.1 [M+H]+.

Workup

  1. customThe crude sample was purified via Biotage normal phase chromatography (25 g SNAP column, 0%-65%, 65%. hex/EtOAc)
  2. additionThe pure product containing-fractions
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-b88e883558e64b349bb1be011b7619c0
Source dataset
uspto-grants-2015_12
Patent number
US09216965B2

Reaction notes

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