Dimethylformamide → 2-Acetoxy-8-(2-oxopropoxy)quinoline

HRID 263963Notes

Reaction equation

HRID 263963 reaction equation
[C:1]([O:4][C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[C:8]([OH:15])[CH:9]=[CH:10][CH:11]=2)[N:6]=1)(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.Cl[CH2:28][C:29](=[O:31])[CH3:30]>C1COCC1>[C:1]([O:4][C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[C:8]([O:15][CH2:28][C:29](=[O:31])[CH3:30])[CH:9]=[CH:10][CH:11]=2)[N:6]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 229959082-Acetoxy-8-hydroxyquinoline

Product 1

HCID 190360332-Acetoxy-8-(2-oxopropoxy)quinolineYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5b (1.02 g, 5 mmol), potassium carbonate (0.69 g, 5 mmol) and dry N,N-dimethylformamide (DMF) (40 ml) was stirred at room temperature for 30 min and then chloroacetone (0.46 g, 5 mmol) in dry THF (10 ml) was added in one portion. The resulting mixture was continued to stir at room temperature for 24 h (monitored by TLC). After this period, it was poured into ice water (100 ml) and the pale yellow solid thus obtained was crystallized from dichloromethane and ether to afford 2-Acetoxy-8-(2-oxopropoxy)quinoline (5c) (0.85 g, 66%). mp: 79°-80° C.; 1H-NMR (CDCl3): δ2.16 (s, 3H, OAc), 2.42 (s, 3H, 3'-CH3), 4.85 (s, 2H, OCH2), 7.06 (d, 3-H), 7.26-7.67 (m, 3H, Ar--H), 8.08 (d, 4-H).

Workup

  1. stirringto stir at room temperature for 24 h (monitored by TLC)
  2. waitAfter this period
  3. customthe pale yellow solid thus obtained
  4. customwas crystallized from dichloromethane and ether

Sources & evidence

ORD record
ord-faa03fb378074c8cb06b5f8f345fdfd2
Source dataset
uspto-grants-1997_07
Patent number
US05646164

Reaction notes

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