Acetic Acid → HCID 67435858, compound

HRID 1663375Notes

Reaction equation

HRID 1663375 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][C:5]([CH:11]2[C:20]3[C:19](=[O:21])[CH2:18][CH:17]([CH2:22][CH2:23][CH3:24])[CH2:16][C:15]=3[NH:14][C:13]([CH3:25])=[C:12]2[C:26]#[N:27])=[CH:4][C:3]=1[Br:28].C(O)(=O)C>C1COCC1.[Zn]>[NH2:8][C:7]1[CH:6]=[C:5]([CH:11]2[C:20]3[C:19](=[O:21])[CH2:18][CH:17]([CH2:22][CH2:23][CH3:24])[CH2:16][C:15]=3[NH:14][C:13]([CH3:25])=[C:12]2[C:26]#[N:27])[CH:4]=[C:3]([Br:28])[C:2]=1[NH2:1]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 67434333HCID 67434333, compound

Product 1

HCID 67435858HCID 67435858, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

4-(4-Amino-3-bromo-5-nitro-phenyl)-2-methyl-5-oxo-7-propyl-1,4,5,6,7,8-hexahydro-quinoline-3-carbonitrile (600 mg) was dissolved in THF (150 ml) and cooled to 0° C. Acetic acid (1.3 ml) was added, followed by addition of zinc dust (2 g). The resulting slurry was stirred at 0° C. for 2 h, and then another 4 h at room temperature. The mixture was filtered and diluted with saturated aq. NaHCO3, followed by extraction with ethyl acetate. The organic layer was dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by chromatography on silicagel in heptane/ethyl acetate 3/1→0/1 (v/v) as eluent.

Workup

  1. customanother 4 h
  2. customat room temperature
  3. filtrationThe mixture was filtered
  4. additiondiluted with saturated aq. NaHCO3
  5. extractionfollowed by extraction with ethyl acetate
  6. dry with materialThe organic layer was dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by chromatography on silicagel in heptane/ethyl acetate 3/1→0/1 (v/v) as eluent

Sources & evidence

ORD record
ord-48e8b5bab6884cbca9b08b3619c569f5
Source dataset
uspto-grants-2011_10
Patent number
US08034945B2

Reaction notes

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