Sodium Nitrite → 6-Fluoro-isoquinoline-3-carbonyl azide

HRID 340883ノート

反応式

HRID 340883 の反応式
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[N:7][C:6]([C:12]([NH:14][NH2:15])=[O:13])=[CH:5]2.[N:16]([O-])=O.[Na+]>Cl.O>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[N:7][C:6]([C:12]([N:14]=[N+:15]=[N-:16])=[O:13])=[CH:5]2

参加物

5

反応物 2

HCID 23668193Sodium Nitrite2 回HCID 579481706-Fluoroisoquinoline-3-carbohydrazide

生成物 1

HCID 579473966-Fluoro-isoquinoline-3-carbonyl azide収率 89%

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒HCID 962Water溶媒3 回

反応条件

温度
2.5 °C

実験手順

To a suspension of 6-fluoro-isoquinoline-3-carboxylic acid hydrazide in HCl (1 N, 50 mL) and water (1 L) was added a solution of NaNO2 (11.4 g, 170 mmol, 1.5 eq) in water (100 mL) dropwise at 0-5° C. The mixture was stirred at 0-5° C. for 1 h. Another solution of NaNO2 (5.7 g, 85 mmol, 0.5 equiv.) in water (30 mL) was added and the reaction was stirred at 0-5° C. for 3 h until LC-MS indicated the completion of the reaction. The precipitate was filtered, washed with cold water, and dried under high vacuum to give 6-fluoro-isoquinoline-3-carbonyl azide as a light yellow solid (21.3 g, 89%). LRMS (M+H+) m/z 217.1.

後処理

  1. stirringthe reaction was stirred at 0-5° C. for 3 h until LC-MS
  2. customthe completion of the reaction
  3. filtrationThe precipitate was filtered
  4. washwashed with cold water
  5. customdried under high vacuum

出典と根拠

ORDレコード
ord-2a4d9b263af54068a3272ba262ed499f
出典データセット
uspto-grants-2014_11
特許番号
US08895582B2

反応ノート

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