Potassium Hydroxide → HCID 10270013, compound

HRID 917311Notes

Reaction equation

HRID 917311 reaction equation
[OH-].[K+].C([O:5][C:6]([CH:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:15]=[C:16]3[C:21](=[C:22]([C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([O:30][CH3:31])[CH:25]=4)[N:23]=2)[N:20]=[CH:19][CH:18]=[CH:17]3)[CH2:10][CH2:9]1)=[O:7])C>C1COCC1.C(O)C.C(OCC)(=O)C>[CH3:31][O:30][C:26]1[CH:25]=[C:24]([C:22]2[N:23]=[C:14]([CH:11]3[CH2:10][CH2:9][CH:8]([C:6]([OH:7])=[O:5])[CH2:13][CH2:12]3)[CH:15]=[C:16]3[C:21]=2[N:20]=[CH:19][CH:18]=[CH:17]3)[CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 69398748HCID 69398748, compound

Product 1

HCID 10270013HCID 10270013, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21873804Tetrahydrofuran ethanolSolvent

Conditions

Temperature
80 °C

Procedure

Potassium hydroxide (2 M, 0.9 ml) is added to a solution of 4-[8-(3-Methoxy-phenyl)-[1,7]naphthyridin-6-yl]-cyclohexanecarboxylic acid ethyl ester (230 mg, 0.6 mmol) in THF/ethanol (6 ml:2 ml) and heated at 80° C. for 3 hours. The solution is then diluted with ethyl acetate (120 ml) and extracted with water. The aqueous layer is taken to pH 4 with 1M HCl to give a white precipitate, which is extracted into dichloromethane (DCM). The DCM layer is washed with water, then dried over magnesium sulfate, filtered and concentrated to yield the desired product. M.p 209-212° C. MS (AP+) 362.9

Workup

  1. extractionextracted with water
  2. customto give a white precipitate, which
  3. extractionis extracted into dichloromethane (DCM)
  4. washThe DCM layer is washed with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-59af0b6d8b254b85bf28fa4fa0dba2db
Source dataset
uspto-grants-2007_09
Patent number
US07273875B2

Reaction notes

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