Phosphorus oxychloride → 6-(Benzyloxy)-4-chloro-7-methoxy-3-nitroquinoline

HRID 1467378Notes

Reaction equation

HRID 1467378 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][C:18]=1[O:19][CH3:20])[NH:15][CH:14]=[C:13]([N+:21]([O-:23])=[O:22])[C:12]2=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:27])=O>CN(C)C=O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][C:18]=1[O:19][CH3:20])[N:15]=[CH:14][C:13]([N+:21]([O-:23])=[O:22])=[C:12]2[Cl:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 866891776-(Benzyloxy)-7-methoxy-3-nitroquinolin-4(1H)-one

Product 1

HCID 666119326-(Benzyloxy)-4-chloro-7-methoxy-3-nitroquinolineYield 99.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

6-Benzyloxy-7-methoxy-3-nitro-1H-quinolin-4-one (9.10 g, 27.89 mmol, see Acta Pharmacologica Sinica 2008, 29(12), 1529-1538) was suspended in dry N,N-dimethylformamide (70 ml). Phosphoryl chloride (2.82 ml, 30.68 mmol) was subsequently added, and the mixture was heated at 100° C. for 30 min. After cooling, the reaction mixture was added to ice-water (500 ml) with stirring and stirred for a further 30 min. The precipitate formed was filtered off with suction, washed with water and dried in vacuo, giving 6-benzyloxy-4-chloro-7-methoxy-3-nitroquinoline (9.57 g, 27.76 mmol) as solid. MS: 345.1 (M+H+), TLC (HPTLC): Rf=0.44 (cyclohexane/ethyl acetate 2:1, parts by volume).

Workup

  1. temperatureAfter cooling
  2. stirringstirred for a further 30 min
  3. customThe precipitate formed
  4. filtrationwas filtered off with suction
  5. washwashed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-fe83a1edf35a444caeb396127a06c876
Source dataset
uspto-grants-2015_04
Patent number
US09000153B2

Reaction notes

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