Hydrochloric Acid → 5-Amino-3,4-dihydronaphthalen-1(2H)-one

HRID 719170ノート

反応式

HRID 719170 の反応式
[CH2:1]1[CH2:11][C:9](=[O:10])[C:8]2[C:3](=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:2]1.Cl.[N:13]([O-])=O.[Na+].[N-:17]=[N+:18]=[N-:19].[Na+]>O>[NH2:13][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:3]=1[CH2:2][CH2:1][CH2:11][C:9]2=[O:10].[N:17]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:3]=1[CH2:2][CH2:1][CH2:11][C:9]2=[O:10])=[N+:18]=[N-:19]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 107241-TetraloneHCID 33557Sodium AzideHCID 23668193Sodium Nitrite

生成物 2

HCID 115065055-Amino-3,4-dihydronaphthalen-1(2H)-oneHCID 218968435-Azido-3,4-dihydro-1(2H)-naphthalenone

試薬・触媒・溶媒 1

HCID 962Water溶媒3 回

実験手順

5-Amino-1-tetralone was prepared from α-tetralone according to the literature (J. Am. Chem. Soc. 1994, p4852). To a cold solution of 5-amino-1-tetratone (415 mg) in water (2 mL) and concentrated hydrochloric acid (5 mL) was added a solution of sodium nitrite (186 mg) in water (1.2 mL), maintaining low temperature. After 40 minutes a solution of sodium azide (184 mg) in water (1.2 mL) was added dropwise. The reaction mixture was allowed to warm to room temperature. After one further hour the reaction was quenched with water, extracted into ether, washed with sodium bicarbonate solution, dried (MgSO4) and the solvent removed in vacuo to yield crude material which was purified using flash chromatography to yield 5-azido-1-tetralone (77 mg).

後処理

  1. temperaturemaintaining low temperature
  2. customAfter one further hour the reaction was quenched with water
  3. extractionextracted into ether
  4. washwashed with sodium bicarbonate solution
  5. dry with materialdried (MgSO4)
  6. customthe solvent removed in vacuo
  7. customto yield crude material which
  8. customwas purified

出典と根拠

ORDレコード
ord-8b43ea73b55143e7b5f0d2d6afb116f7
出典データセット
uspto-grants-2006_11
特許番号
US07132419B2

反応ノート

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