Acetic Acid → HCID 67435102, compound

HRID 1663382Notes

Reaction equation

HRID 1663382 reaction equation
C[O:2][C:3](=[O:38])[C:4]1[CH:9]=[C:8]([CH:10]2[C:19]3[C:18](=[O:20])[CH2:17][CH:16]([CH2:21][CH2:22][CH3:23])[CH2:15][C:14]=3[NH:13][C:12]([CH3:24])=[C:11]2[C:25]#[N:26])[CH:7]=[C:6]([Br:27])[C:5]=1[O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([O:36][CH3:37])[CH:31]=1.C(O)(=O)C>O1CCOCC1.[OH-].[Na+]>[Br:27][C:6]1[C:5]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([O:36][CH3:37])[CH:31]=2)=[C:4]([CH:9]=[C:8]([CH:10]2[C:19]3[C:18](=[O:20])[CH2:17][CH:16]([CH2:21][CH2:22][CH3:23])[CH2:15][C:14]=3[NH:13][C:12]([CH3:24])=[C:11]2[C:25]#[N:26])[CH:7]=1)[C:3]([OH:38])=[O:2]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 674350333-Bromo-5-(3-cyano-2-methyl-5-oxo-7-propyl-1,4,5,6,7,8-hexahydro-quinolin-4-yl)-2-(3-methoxy-benzyloxy)-benzoic acid methyl ester

Product 1

HCID 67435102HCID 67435102, compound

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 3-bromo-5-(3-cyano-2-methyl-5-oxo-7-propyl-1,4,5,6,7,8-hexahydro-quinolin-4-yl)-2-(3-methoxy-benzyloxy)-benzoic acid methyl ester (5.7 g) in dioxane (135 ml) and 1N NaOH (15 ml) was stirred for 17 h. The mixture was acidified with conc. acetic acid and extracted with ethyl acetate. The organic layer was dried (MgSO4), filtered and concentrated in vacuo. The residue was dissolved in ethanol and then concentrated until a solid precipitated. The solid was collected by filtration and washed with petroleum ether.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue was dissolved in ethanol
  6. concentrationconcentrated until a solid
  7. customprecipitated
  8. filtrationThe solid was collected by filtration
  9. washwashed with petroleum ether

Sources & evidence

ORD record
ord-efeebd5b86244cb68436b770e3346015
Source dataset
uspto-grants-2011_10
Patent number
US08034945B2

Reaction notes

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