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

HRID 2194939Notes

Reaction equation

HRID 2194939 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent2×

Conditions

Temperature
20 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-83888e9eff374faeaf820c1a632ac846
Source dataset
uspto-grants-2012_12
Patent number
US08334315B2

Reaction notes

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