HCID 67442490, compound → HCID 67440759, compound

HRID 2045240Notes

Reaction equation

HRID 2045240 reaction equation
[CH3:1][C:2]1([CH3:25])[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:12]([F:15])([F:14])[F:13])[CH:9]=2)[NH:4][CH:3]1[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([N+:22]([O-])=O)[CH:17]=1>C(O)C.Cl.[Fe]>[CH3:1][C:2]1([CH3:25])[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:12]([F:15])([F:13])[F:14])[CH:9]=2)[NH:4][CH:3]1[C:16]1[CH:17]=[C:18]([NH2:22])[CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 1

HCID 67442490HCID 67442490, compound

Product 1

HCID 67440759HCID 67440759, compoundYield 86%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Conditions

Temperature
95 °C

Procedure

To a mixture of 3,3-dimethyl-2-(3-nitro-phenyl)-6-trifluoromethyl-1,2,3,4-tetrahydro-quinoline (2.4 g, 6.8 mmol) in ethanol 95% (100 mL) and 10% hydrochloric acid (5 mL) was added iron (1.2 g, 20 mmol). The reaction mixture was stirred at 95° C. for 3 h. Then the insoluble solid was filtered off and the filtrate was concentrated in vacuo and the residue was extracted with ethyl acetate (2×200 mL), washed with 30% sodium hydroxide in water (2×100 mL), dried over anhydrous sodium sulfate and concentrated in vacuo to afford 3-(3,3-dimethyl-6-trifluoromethyl-1,2,3,4-tetrahydro-quinolin-2-yl)-phenylamine (1.8 g, 86%) as a brown solid: LC/MS m/e calcd for C18H19F3N2 (M+H)+: 321.36, observed: 321.1.

Workup

  1. filtrationThen the insoluble solid was filtered off
  2. concentrationthe filtrate was concentrated in vacuo
  3. extractionthe residue was extracted with ethyl acetate (2×200 mL)
  4. washwashed with 30% sodium hydroxide in water (2×100 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7c0872a2a20a4972bc54b74aaf403113
Source dataset
uspto-grants-2013_11
Patent number
US08586747B2

Reaction notes

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