Hydrogen Bromide → HCID 15634792、化合物

HRID 2231284ノート

反応式

HRID 2231284 の反応式
N[C:2]1[C:3]([N+:14]([O-:16])=[O:15])=[CH:4][C:5]2[O:10][C:9]([CH3:12])([CH3:11])[CH:8]=[CH:7][C:6]=2[CH:13]=1.N([O-])=O.[Na+].O.[BrH:22]>C(O)(=O)C.OS(O)(=O)=O>[Br:22][C:2]1[C:3]([N+:14]([O-:16])=[O:15])=[CH:4][C:5]2[O:10][C:9]([CH3:12])([CH3:11])[CH:8]=[CH:7][C:6]=2[CH:13]=1

参加物

7

反応物 4

HCID 260Hydrogen BromideHCID 962WaterHCID 132228932,2-Dimethyl-7-nitro-2H-chromen-6-amineHCID 23668193Sodium Nitrite

生成物 1

HCID 15634792HCID 15634792、化合物

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 1118Sulfuric Acid溶媒

実験手順

A suspension of 6-amino-2,2-dimethyl-7-nitro-2H-1-benzopyran (5.0 g, the preparation of which was described in J. Med. Chem., 26, 1582 (1983)) in glacial acetic acid (19 mL) was added dropwise to a stirred solution of sodium nitrite (1.6 g) in conc. H2SO4 (19 mL) while maintaining the temperature below 10° C. After an additional 0.5 h, the dark brown solution was added to a stirred solution of CuBr (6.5 g) in 47% HBr (53 mL). After 1 h, water was added to the solution and it was extracted with ethyl acetate. The organic extract was washed with water, saturated sodium bicarbonate solution, and dried over anh. MgSO4. The organic layer was filtered, evaporated, and chromatographed on silica gel. Elution with 3% ethyl acetate--60°-80° C. petroleum ether gave the compound of description 1 as a crude solid (3.5 g). Mass spectrum (E.I.) M+ at m/z 282.9848. Calcd. for C11H10NO3Br: 282.9845.

後処理

  1. customthe preparation of which
  2. temperaturewhile maintaining the temperature below 10° C
  3. waitAfter 1 h
  4. extractionwas extracted with ethyl acetate
  5. extractionThe organic extract
  6. washwas washed with water, saturated sodium bicarbonate solution
  7. dry with materialdried over anh. MgSO4
  8. filtrationThe organic layer was filtered
  9. customevaporated
  10. customchromatographed on silica gel
  11. washElution with 3% ethyl acetate--60°-80° C. petroleum ether

出典と根拠

ORDレコード
ord-62d9918e45f043648a127807046cea1b
出典データセット
uspto-grants-1988_11
特許番号
US04782083

反応ノート

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