Acetic Acid → HCID 67435247, compound

HRID 1663370Notes

Reaction equation

HRID 1663370 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:23]2[C:32]3[C:31](=[O:33])[CH2:30][CH:29]([CH2:34][CH2:35][CH3:36])[CH2:28][C:27]=3[NH:26][C:25]([CH3:37])=[C:24]2[C:38]#[N:39])[CH:7]=[C:8]([N+:20]([O-])=O)[C:9]=1[O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=1)[CH3:2].C(O)(=O)C>C1COCC1.[Zn]>[NH2:20][C:8]1[CH:7]=[C:6]([CH:23]2[C:32]3[C:31](=[O:33])[CH2:30][CH:29]([CH2:34][CH2:35][CH3:36])[CH2:28][C:27]=3[NH:26][C:25]([CH3:37])=[C:24]2[C:38]#[N:39])[CH:5]=[C:4]([O:3][CH2:1][CH3:2])[C:9]=1[O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 67434623HCID 67434623, compound

Product 1

HCID 67435247HCID 67435247, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-[3-ethoxy-4-(3-methoxy-benzyloxy)-5-nitro-phenyl]-2-methyl-5-oxo-7-propyl-1,4,5,6,7,8-hexahydro-quinoline-3-carbonitrile and acetic acid (1.3 ml) in THF (33 ml) was cooled to 0° C. Zinc dust (3.02 g) was added in portions under vigorous stirring. The mixture was allowed to reach room temperature and stirred for 1 h. The mixture was then filtered and concentrated in vacuo. The residue was dissolved in dichloromethane and washed with sat. aq. NaHCO3. The organic layer was dried (MgSO4), filtered and concentrated in vacuo.

Workup

  1. customto reach room temperature
  2. filtrationThe mixture was then filtered
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was dissolved in dichloromethane
  5. washwashed with sat. aq. NaHCO3
  6. dry with materialThe organic layer was dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f792fb67c5f9453c95fec94c1ba68f77
Source dataset
uspto-grants-2011_10
Patent number
US08034945B2

Reaction notes

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