Water → HCID 59625627, compound

HRID 2192805Notes

Reaction equation

HRID 2192805 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][NH:7][C:8]1[C:17]([C:18]([O:20]CC)=[O:19])=[CH:16][C:15]2[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=2[N:9]=1.O.[OH-].[Na+]>C(O)C>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][NH:7][C:8]1[C:17]([C:18]([OH:20])=[O:19])=[CH:16][C:15]2[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=2[N:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 59625312HCID 59625312, compound

Product 1

HCID 59625627HCID 59625627, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of ethyl 2-[(furan-2-ylmethyl)amino]-5,6,7,8-tetrahydroquinoline-3-carboxylate (600 mg) in ethanol (4 ml)-water (4 ml) was added 8 M aqueous sodium hydroxide solution (1.25 ml), and the mixture was stirred at 80° C. for 10 hr. The reaction mixture was concentrated under reduced pressure to about 1/3 volume, and neutralized with 1 M hydrochloric acid, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give the object compound (522 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure to about 1/3 volume
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-06b77f94b1f24662ae9bb7c743026b43
Source dataset
uspto-grants-2012_12
Patent number
US08329691B2

Reaction notes

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