Sodium Bicarbonate → HCID 19994760, compound

HRID 2248889Notes

Reaction equation

HRID 2248889 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:34]=[CH:33][C:16]([O:17][CH2:18][C:19]2[C:27]3[O:26][C:25]([C:28]([O:30]CC)=[O:29])=[N:24][C:23]=3[CH:22]=[CH:21][CH:20]=2)=[CH:15][CH:14]=1.C(=O)(O)[O-].[Na+]>C(O)C.O>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([O:17][CH2:18][C:19]2[C:27]3[O:26][C:25]([C:28]([OH:30])=[O:29])=[N:24][C:23]=3[CH:22]=[CH:21][CH:20]=2)=[CH:33][CH:34]=1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 19994678HCID 19994678, compound

Product 1

HCID 19994760HCID 19994760, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

0.66 g of ethyl 7-(4-(quinoline-2-ylmethyloxy)phenoxymethyl)benzoxazole-2-carboxylate and 0.7 g sodium bicarbonate are combined in 50 ml of ethanol and 5 ml of water. After refluxing for 1.5 hours the mixture is concentrated and the residue diluted with ether. The resulting solid is collected, suspended in water and the pH adjusted to 6 with 1 molar hydrochloric acid. The resulting solid is crystallized from aqueous acetic acid, then tetrahydrofuran/hexane to give 7-(4-(quinolin-2-ylmethyloxy)phenoxymethyl)benzoxazole-2-carboxylic acid.

Workup

  1. temperatureAfter refluxing for 1.5 hours the mixture
  2. concentrationis concentrated
  3. additionthe residue diluted with ether
  4. customThe resulting solid is collected
  5. customThe resulting solid is crystallized from aqueous acetic acid

Sources & evidence

ORD record
ord-1345185656244f4babaa96ca1389e3b6
Source dataset
uspto-grants-1991_08
Patent number
US05041453

Reaction notes

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