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

HRID 2194939Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2194939
[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

Komponenten

6

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittel2×HCID 962WaterLösungsmittel2×

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-83888e9eff374faeaf820c1a632ac846
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08334315B2

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