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Triethyl Phosphate → 5-Chloro-2,6-dimethoxy-4-methyl-8-nitroquinoline

HRID 1018028
ノート
印刷プレビュー

反応式

HRID 1018028 の反応式
C(OP(OCC)(OCC)=O)C.[CH3:12][O:13][C:14]1[CH:23]=[C:22]([CH3:24])[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([O:26][CH3:27])[C:20]=2[Cl:25])[N:15]=1.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[N+:42]([O-])([O-:44])=[O:43].[K+]>CO>[N+:42]([C:17]1[CH:18]=[C:19]([O:26][CH3:27])[C:20]([Cl:25])=[C:21]2[C:16]=1[N:15]=[C:14]([O:13][CH3:12])[CH:23]=[C:22]2[CH3:24])([O-:44])=[O:43]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 6535Triethyl PhosphateHCID 14812Phosphorus oxide (P4O10)HCID 24434Potassium NitrateHCID 184059815-Chloro-2,6-dimethoxy-4-methylquinoline

生成物 1

HCID 109680055-Chloro-2,6-dimethoxy-4-methyl-8-nitroquinoline収率 68%

試薬・触媒・溶媒 1

HCID 887
Methanol
溶媒

反応条件

温度
37.5 °C

実験手順

A 20-liter reactor equipped with a mechanical stirrer, thermowatch, and condenser was charged with triethylphosphate (6.3 liters) and 2,6-dimethoxy-5-chloro-4-methylquinoline (5) (500 g, 2.11 moles). Phosphorous pentoxide (1.052 kg, 7.11 moles) was added in one portion and the resulting slurry stirred for 60 minutes. Reaction temperature was adjusted to 35° C. and solid potassium nitrate (0.423 kg, 4.21 moles) added in one portion. N-hexane is added and the reaction temperature was maintained at 35-40° C. for 2 hours. Methanol (4.2 liters) was added and the mixture heated to reflux and held for 1 hour. The yellow slurry was cooled to 0-5° C. and held for 2 hours. The product was collected by suction filtration, washed with water to neutral pH, then methanol, air dried and oven dried at 60-70° C. to yield the title compound 350 g (68%); mp 199-200° C.;

後処理

  1. customA 20-liter reactor equipped with a mechanical stirrer
  2. customReaction temperature
  3. customwas adjusted to 35° C.
  4. temperaturethe mixture heated
  5. temperatureto reflux
  6. waitheld for 1 hour
  7. temperatureThe yellow slurry was cooled to 0-5° C.
  8. waitheld for 2 hours
  9. filtrationThe product was collected by suction filtration
  10. washwashed with water to neutral pH
  11. dry with materialmethanol, air dried
  12. customoven dried at 60-70° C.

出典と根拠

ORDレコード
ord-a48012aecff44ec6833a918f6091d8d0
出典データセット
uspto-grants-2002_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06479660B1

反応ノート

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