HCID 67440441, compound → HCID 67440544, compound

HRID 1800973Notes

Reaction equation

HRID 1800973 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[NH:11][CH:10]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-])=O)[CH:16]=1)[C:9]([CH3:25])([CH3:24])[CH2:8]2)(=[O:4])=[O:3]>C(O)C.Cl.[Fe]>[CH3:1][S:2]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[NH:11][CH:10]([C:15]1[CH:16]=[C:17]([NH2:21])[CH:18]=[CH:19][CH:20]=1)[C:9]([CH3:25])([CH3:24])[CH2:8]2)(=[O:4])=[O:3]

Participants

5

Reactant 1

HCID 67440441HCID 67440441, compound

Product 1

HCID 67440544HCID 67440544, compoundYield 62.2%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Conditions

Temperature
95 °C

Procedure

To a mixture of 6-methanesulfonyl-3,3-dimethyl-2-(3-nitro-phenyl)-1,2,3,4-tetrahydro-quinoline (6.5 g, 18 mmol) in ethanol 95% (100 mL) and 10% hydrochloric acid (10 mL) was added iron (3.04 g, 54 mmol). The reaction mixture was stirred at 95° C. for 5 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-methanesulfonyl-3,3-dimethyl-1,2,3,4-tetrahydro-quinolin-2-yl)-phenylamine (3.7 g, 25%) as a yellow solid: LC/MS m/e calcd for C18H22N2O2S (M+H)+: 331.45, observed: 331.1.

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-3dd46d416ade4849b661085e989ede32
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

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