2-Methyl-3-nitroaniline → (2R)-8-Amino-1,2,3,4-tetrahydro-2-naphthalenol

HRID 2194939ノート

反応式

HRID 2194939 の反応式
[CH3:1][C:2]1[C:8]([N+:9]([O-])=O)=[CH:7][CH:6]=[CH:5][C:3]=1N.N([O-])=O.[Na+].C([O:19][CH2:20][CH3:21])(=O)C.[CH3:22]CCCCC>C(O)(=O)C.O>[NH2:9][C:8]1[CH:7]=[CH:6][CH:5]=[C:3]2[C:2]=1[CH2:1][C@H:20]([OH:19])[CH2:21][CH2:22]2

参加物

6

反応物 3

HCID 117832-Methyl-3-nitroanilineHCID 21226206Ethyl acetate hexaneHCID 23668193Sodium Nitrite

生成物 1

HCID 57936087(2R)-8-Amino-1,2,3,4-tetrahydro-2-naphthalenol収率 68%

試薬・触媒・溶媒 2

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

反応条件

温度
20 °C

実験手順

2-methyl-3-nitro aniline (10 g, 0.005 mol) was taken in acetic acid (100 ml, 10 times) and cooled to 20° C. A solution of sodium nitrite (10 g, 0.14 mol, 2.25 eq) in water (25 ml) was added drop wise for 15 min at 20° C. The overall reaction mixture was stirred for 30 min at 20° C. and later stirred for 2 hrs at rt. Progress of the reaction was monitored by TLC (15% ethyl acetate/hexane, Rf˜0.2). On completion of the reaction, acetic acid was distilled off completely and the residue obtained was taken in cold water (200 ml). Solid thrown out was filtered and dried to yield the required product as an yellow colored solid (8.5 g, 68% yield).

後処理

  1. stirringlater stirred for 2 hrs at rt
  2. distillationwas distilled off completely
  3. customthe residue obtained
  4. filtrationSolid thrown out was filtered
  5. customdried

出典と根拠

ORDレコード
ord-83888e9eff374faeaf820c1a632ac846
出典データセット
uspto-grants-2012_12
特許番号
US08334315B2

反応ノート

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