HCID 67441923, compound → HCID 67441715, compound

HRID 1800935Notes

Reaction equation

HRID 1800935 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-])=O)[CH:13]=1)[C:6]([CH3:22])([CH3:21])[CH2:5]2>C(O)C.Cl.[Fe]>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]([C:12]1[CH:13]=[C:14]([NH2:18])[CH:15]=[CH:16][CH:17]=1)[C:6]([CH3:22])([CH3:21])[CH2:5]2

Participants

5

Reactant 1

HCID 67441923HCID 67441923, compound

Product 1

HCID 67441715HCID 67441715, compoundYield 82.4%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Conditions

Temperature
95 °C

Procedure

To a mixture of 6-chloro-3,3-dimethyl-2-(3-nitro-phenyl)-1,2,3,4-tetrahydro-quinoline (10.5 g, 33 mmol) in ethanol 95% (150 mL) and 10% hydrochloric acid (10 mL) was added iron (3.72 g, 66 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-(6-chloro-3,3-dimethyl-1,2,3,4-tetrahydro-quinolin-2-yl)-phenylamine (7.8 g, 82%) as a yellow solid: LC/MS m/e calcd for C17H19ClN2 (M+H)+: 287.81, observed: 287.0.

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-50cd95de1c7542c7bf17805defd2f8ea
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

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