Acetic Acid → HCID 67410110, compound

HRID 909387Notes

Reaction equation

HRID 909387 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([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:6]([O:19][CH:20]([CH3:22])[CH3:21])[C:7]=1[O:8]CC1C=CC([N+]([O-])=O)=CC=1.C(O)(=O)C>C1COCC1.[Zn]>[Br:1][C:2]1[CH:3]=[C:4]([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:6]([O:19][CH:20]([CH3:22])[CH3:21])[C:7]=1[OH:8]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 674132084-[3-Bromo-5-isopropoxy-4-(4-nitro-benzyloxy)-phenyl]-2-methyl-5-oxo-7-propyl-1,4,5,6,7,8-hexahydro-quinoline-3-carbonitrile

Product 1

HCID 67410110HCID 67410110, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product isolated in step c (750 mg) and acetic acid (1.5 ml) in THF (50 ml) was added zinc dust (1.5 g) under vigorous stirring. The mixture was stirred for 2 h and then filtered. The mixture was diluted with EtOAc and washed with sat. aq. NaHCO3. The organic layer was dried (MgSO4), filtered and concentrated in vacuo.

Workup

  1. filtrationfiltered
  2. additionThe mixture was diluted with EtOAc
  3. washwashed with sat. aq. NaHCO3
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-09c347ce1ad143619084111af8d1777c
Source dataset
uspto-grants-2011_09
Patent number
US08017782B2

Reaction notes

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