Hydrochloric Acid → 5-methyl-5H-pyrido[3,4-f]pyrrolo[1,2-b][1,2,5]triazepine

HRID 1638378ノート

反応式

HRID 1638378 の反応式
Cl.[CH3:2][N:3]([N:13]1[CH:17]=[CH:16][CH:15]=[C:14]1[CH:18]=O)[C:4]1[CH:9]=[CH:8][N:7]=[CH:6][C:5]=1[N+:10]([O-])=O.[OH-].[Na+]>O1CCCC1>[CH3:2][N:3]1[C:4]2[CH:9]=[CH:8][N:7]=[CH:6][C:5]=2[N:10]=[CH:18][C:14]2=[CH:15][CH:16]=[CH:17][N:13]12

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 142321061-[N-methyl-N-(3-nitro-4-pyridinyl)amino]pyrrole-2-carboxaldehyde2 回

生成物 1

HCID 146019475-methyl-5H-pyrido[3,4-f]pyrrolo[1,2-b][1,2,5]triazepine収率 44.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To cold, concentrated hydrochloric acid (200 ml) was added, in the following order, 100 g of stannous chloride dihydrate, 200 ml of tetrahydrofuran, and a solution of 28 g of 1-[N-methyl-N-(3-nitro-4-pyridinyl)amino]pyrrole-2-carboxaldehyde in 150 ml of tetrahydrofuran. Upon completion of the 1-[N-methyl-N-(3-nitro-4-pyridinyl)amino]pyrrole-2-carboxaldehyde addition, the reaction was poured into an aqueous solution of sodium hydroxide (200 g in 1 liter of water), stirred for five minutes, and then extracted with ethyl acetate. The organic layer was washed with water followed by a saturated sodium chloride solution, dried over anhydrous magnesium sulfate, filtered, and concentrated. The resultant oil was purified by means of high pressure liquid chromatography (silica gel; elution with ethyl acetate) to afford 10 g (38%) of 5-methyl-5H-pyrido[3,4-f]pyrrolo[1,2-b][1,2,5]triazepine as an oil, IR(CHCl3) C=N @ 1610 cm-1 ; MS(EI) M+ @ 199(100%).

後処理

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resultant oil was purified by means of high pressure liquid chromatography (silica gel; elution with ethyl acetate)

出典と根拠

ORDレコード
ord-4dcc56ce61504b2e833fee38f9cf5e92
出典データセット
uspto-grants-1989_11
特許番号
US04879382

反応ノート

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