Stannous Chloride → Ethyl 4-(5-amino-3-methyl-4-oxo-1,4-dihydroquinolin-8-yl)cyclohex-3-ene-1-carboxylate

HRID 1948112Notes

Reaction equation

HRID 1948112 reaction equation
[CH3:1][C:2]1[C:11](=[O:12])[C:10]2[C:5](=[C:6]([C:16]3[CH2:21][CH2:20][CH:19]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:18][CH:17]=3)[CH:7]=[CH:8][C:9]=2[N+:13]([O-])=O)[NH:4][CH:3]=1.Cl[Sn]Cl>CCO>[NH2:13][C:9]1[CH:8]=[CH:7][C:6]([C:16]2[CH2:21][CH2:20][CH:19]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:18][CH:17]=2)=[C:5]2[C:10]=1[C:11](=[O:12])[C:2]([CH3:1])=[CH:3][NH:4]2

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 67254537Ethyl 4-(3-methyl-5-nitro-4-oxo-1,4-dihydroquinolin-8-yl)cyclohex-3-ene-1-carboxylate2×

Product 1

HCID 67254617Ethyl 4-(5-amino-3-methyl-4-oxo-1,4-dihydroquinolin-8-yl)cyclohex-3-ene-1-carboxylateYield 49%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl 4-(3-methyl-5-nitro-4-oxo-1,4-dihydroquinolin-8-yl)cyclohex-3-ene-1-carboxylate (Compound 304D, 600 mg, 1.69 mmol) in EtOH (50 mL) was charged with SnCl2 (1.2 g, 5.33 mmol). The resulting mixture was stirred under reflux for 18 h. The reaction mixture was concentrated under reduced pressure. The residue was quenched with aq. NaHCO3 solution (500 mL) and extracted with EtOAc (3×200 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure. The material was purified by prep TLC to afford the desired compound (270 mg, yield: 49%). 1H NMR (CDCl3, 400 MHz): δ=1.22 (t, J=7.2 Hz, 3H), 1.99 (s, 3H), 2.03 (m, 1H), 2.11-2.13 (m, 2H), 2.19-2.21 (m, 2H), 2.34-2.39 (m, 2H), 2.78 (m, 1H), 3.42 (d, J=3.2 Hz, 1H), 4.12 (q, J=7.2 Hz, 2H), 5.71 (s, 1H), 6.20 (d, J=8.0 Hz, 1H), 6.71 (s, br, 2H), 6.93 (d, J=8.0 Hz, 1H), 7.36 (d, J=6.0 Hz, 1H), 8.91 (s, br, 1H).

Workup

  1. temperatureunder reflux for 18 h
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customThe residue was quenched with aq. NaHCO3 solution (500 mL)
  4. extractionextracted with EtOAc (3×200 mL)
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe material was purified by prep TLC

Sources & evidence

ORD record
ord-c66d9fee9a0c4ca4a871375fc1487293
Source dataset
uspto-grants-2013_03
Patent number
US08399433B2

Reaction notes

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