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Sulfuric Acid → 6-Methoxyphthalazin-1-ol

HRID 2297399
ノート
印刷プレビュー

反応式

HRID 2297399 の反応式
CC1(C)C[O:5][C:4]([C:7]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][C:8]=2[CH:9]=O)=[N:3]1.OS(O)(=O)=O.O.[NH2:24]N.C([O-])(O)=O.[Na+]>C(O)(=O)C.O.C(O)C>[CH3:16][O:15][C:12]1[CH:11]=[C:8]2[C:7](=[CH:14][CH:13]=1)[C:4](=[O:5])[NH:3][N:24]=[CH:9]2
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 1118Sulfuric AcidHCID 24654Hydrazine hydrate (1:1)HCID 516892Sodium BicarbonateHCID 122201362-(4,4-Dimethyl-4,5-dihydro-oxazol-2-yl)-5-methoxy-benzaldehyde

生成物 1

HCID 122985436-Methoxyphthalazin-1-ol収率 73.4%

試薬・触媒・溶媒 3

HCID 176Acetic Acid
溶媒
HCID 702Ethanol溶媒2 回
HCID 962Water溶媒2 回

実験手順

A solution of 2-(4,4-dimethyl-4,5-dihydro-oxazol-2-yl)-5-methoxy-benzaldehyde (2 g, 8.58 mmoles), prepared as described in example 2, in 30 ml of a mixture of water (5 ml), ethanol (50 ml) and concentrated H2SO4 (4 ml) up to 100 ml with ethanol, was stirred under reflux for 20 hours, then concentrated to small volume, taken up in water, extracted with ethyl ether and the organic phase was washed with water, anhydrified and brought to dryness. The resultant oil was dissolved in acetic acid (14 ml) and dropwise added, under N2, with hydrazine monohydrate (1.25 ml, 25.7 mmoles) dissolved in acetic acid (6 ml). The mixture was stirred for 3.5 hours at room temperature, then at 80° C. for 4 hours, then cooled, brought to almost complete dryness, taken up in water, neutralised with NaHCO3, extracted more times with CH2Cl2. The organic phases were washed with water, anhydrified and concentrated. The residue was triturated in CH2Cl2 (10 ml) and filtered to give 1.1 g of the title compound (yield: 73.4%). m.p.: 200-205° C.

後処理

  1. temperatureunder reflux for 20 hours
  2. concentrationconcentrated to small volume
  3. extractionextracted with ethyl ether
  4. washthe organic phase was washed with water
  5. dissolutionThe resultant oil was dissolved in acetic acid (14 ml)
  6. stirringThe mixture was stirred for 3.5 hours at room temperature
  7. temperaturecooled
  8. extractionextracted more times with CH2Cl2
  9. washThe organic phases were washed with water, anhydrified
  10. concentrationconcentrated
  11. customThe residue was triturated in CH2Cl2 (10 ml)
  12. filtrationfiltered

出典と根拠

ORDレコード
ord-961de4e9f1bc424fa1bbe620207fde06
出典データセット
uspto-grants-2002_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06492360B1

反応ノート

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