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

HRID 2194939노트

반응식

HRID 2194939 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 176Acetic Acid용매2회HCID 962Water용매2회

반응 조건

온도
20 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-83888e9eff374faeaf820c1a632ac846
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08334315B2

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