Hydrochloric Acid → HCID 21469272, compound

HRID 1938354Notes

Reaction equation

HRID 1938354 reaction equation
[OH:1][CH:2]([CH2:8][C:9]1[CH:10]=[N:11][C:12]2[C:17]([CH:18]=1)=[CH:16][CH:15]=[C:14]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH:13]=2)[C:3](OCC)=[O:4].[NH2:27][C:28](N)=[O:29].C[O-].[Na+].C(=O)([O-])O.[Na+].Cl>C(O)C.O>[CH2:20]([O:19][C:14]1[CH:13]=[C:12]2[C:17]([CH:18]=[C:9]([CH2:8][CH:2]3[O:1][C:28](=[O:29])[NH:27][C:3]3=[O:4])[CH:10]=[N:11]2)=[CH:16][CH:15]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 1176UreaHCID 516892Sodium BicarbonateHCID 10942334Sodium MethoxideHCID 21469302HCID 21469302, compound

Product 1

HCID 21469272HCID 21469272, compoundYield 68.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

In ethanol (1.5 mL) were suspended ethyl 2-hydroxy-3-(7-benzyloxy-3-quinolyl)propionate (162 mg, 0.461 mmol.), urea (48.7 mg, 0.804 mmol.) and sodium methoxide (28% methanolic solution, 0.12 mL, 0.622 mmol.). The resulting suspension was stirred for one hour at room temperature, and then heated under reflux for 4 hours. The reaction mixture was cooled, and neutralized by addition of saturated aqueous sodium hydrogen carbonate solution after addition of 1N hydrochloric acid (1.0 mL) and water (2.0 mL). Insolubles were collected, washed with ethyl acetate and ether, and dried under reduced pressure, to give 110 mg of the desired compound as white crystalline powder (yield 66%).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 4 hours
  3. temperatureThe reaction mixture was cooled
  4. customInsolubles were collected
  5. washwashed with ethyl acetate and ether
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-e73a3ebef9c84e9f857966833175a666
Source dataset
uspto-grants-1997_12
Patent number
US05693651

Reaction notes

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