Potassium Carbonate → Ethyl 6-nitro-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylate

HRID 1448469ノート

反応式

HRID 1448469 の反応式
Br[CH:2]([CH2:8]Br)[C:3]([O:5][CH2:6][CH3:7])=[O:4].C(=O)([O-])[O-].[K+].[K+].[N+:16]([C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[C:21]([NH2:26])[CH:20]=1)([O-:18])=[O:17]>CC(C)=O>[N+:16]([C:19]1[CH:24]=[CH:23][C:22]2[O:25][CH:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH2:8][NH:26][C:21]=2[CH:20]=1)([O-:18])=[O:17]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 97945Ethyl 2,3-dibromopropionateHCID 36133892-Amino-4-Nitrophenol

生成物 1

HCID 20379906Ethyl 6-nitro-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylate

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

29.2 g of ethyl 2,3-dibromopropionate was added dropwise to a refluxing mixture of 19 g of anhydrous potassium carbonate, 70.9 g of 4-nitro-2-aminophenol and 500 ml of dry acetone. This procedure was repeated thrice. The reaction mixture was refluxed for 17 hours, then filtered. The solvent was evaporated from the filtrate under reduced pressure. The residue was washed with dilute sodium hydroxide solution, extracted with ether, then with methylene chloride. The solvent was evaporated separately from each extract. Thin layer chromatographic analysis indicated that the produce from each of the extracts was the same. The products was combined and recrystallized from ether to give 4, as a solid, m.p.: 88°-90° C.

後処理

  1. temperatureThe reaction mixture was refluxed for 17 hours
  2. filtrationfiltered
  3. customThe solvent was evaporated from the filtrate under reduced pressure
  4. washThe residue was washed with dilute sodium hydroxide solution
  5. extractionextracted with ether
  6. customThe solvent was evaporated separately from each extract
  7. customproduce from each of the extracts
  8. customrecrystallized from ether
  9. customto give 4

出典と根拠

ORDレコード
ord-b80a57ffdb0d48b480d5b1fd6211d4a3
出典データセット
uspto-grants-1979_12
特許番号
US04180572

反応ノート

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