HCID 67289100, compound → 3-(4,4-Dimethyl-6-trifluoromethyl-1,2,3,4-tetrahydro-quinolin-2-yl)-phenylamine

HRID 1036939Notes

Reaction equation

HRID 1036939 reaction equation
[CH3:1][C:2]1([CH3:25])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([F:15])([F:14])[F:13])[CH:10]=2)[NH:5][CH:4]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([N+:22]([O-])=O)[CH:17]=2)[CH2:3]1>C(O)C.O.[Fe]>[CH3:1][C:2]1([CH3:25])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([F:15])([F:13])[F:14])[CH:10]=2)[NH:5][CH:4]([C:16]2[CH:17]=[C:18]([NH2:22])[CH:19]=[CH:20][CH:21]=2)[CH2:3]1

Participants

4

Reactant 1

HCID 67289100HCID 67289100, compound

Product 1

HCID 672916153-(4,4-Dimethyl-6-trifluoromethyl-1,2,3,4-tetrahydro-quinolin-2-yl)-phenylamineYield 95.6%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Procedure

A mixture of 4,4-dimethyl-2-(3-nitro-phenyl)-6-trifluoromethyl-1,2,3,4-tetrahydro-quinoline (2.99 g, 8.53 mmol) and iron powder (11.95 g, 0.21 mol) in ethanol/water/concentrated hydrogen chloride (24 mL/6 mL/0.08 mL) was kept at reflux for 2 h. The mixture was filtered and the mother liquor was concentrated in vacuo to give 2.6 g of 3-(4,4-dimethyl-6-trifluoromethyl-1,2,3,4-tetrahydro-quinolin-2-yl)-phenylamine as off-yellow solid (2.6 g, yield: 95.6%).

Workup

  1. temperatureat reflux for 2 h
  2. filtrationThe mixture was filtered
  3. concentrationthe mother liquor was concentrated in vacuo

Sources & evidence

ORD record
ord-8d68fdc315b4404fa00bf384a2027754
Source dataset
uspto-grants-2013_10
Patent number
US08546427B2

Reaction notes

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