Ethanol → 2-carboxy-5-hydroxy-3-(4-methoxyphenyl)7-(4-(quinolin-2-ylmethoxy)benzyloxy)-4-oxo-4H-1H-benzopyran

HRID 1110914Notes

Reaction equation

HRID 1110914 reaction equation
[C:1]([C:6]1[O:7][C:8]2[CH:24]=[C:23]([O:25][CH2:26][C:27]3[CH:32]=[CH:31][C:30]([O:33][CH2:34][C:35]4[CH:44]=[CH:43][C:42]5[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=5)[N:36]=4)=[CH:29][CH:28]=3)[CH:22]=[C:21]([OH:45])[C:9]=2[C:10](=[O:20])[C:11]=1[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)([O:3]CC)=[O:2].C(=O)(O)[O-].[Na+].C(O)C>O>[C:1]([C:6]1[O:7][C:8]2[CH:24]=[C:23]([O:25][CH2:26][C:27]3[CH:32]=[CH:31][C:30]([O:33][CH2:34][C:35]4[CH:44]=[CH:43][C:42]5[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=5)[N:36]=4)=[CH:29][CH:28]=3)[CH:22]=[C:21]([OH:45])[C:9]=2[C:10](=[O:20])[C:11]=1[C:12]1[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=1)([OH:3])=[O:2]

Participants

5

Reactant 3

HCID 702EthanolHCID 516892Sodium BicarbonateHCID 19913832HCID 19913832, compound

Product 1

HCID 199138612-carboxy-5-hydroxy-3-(4-methoxyphenyl)7-(4-(quinolin-2-ylmethoxy)benzyloxy)-4-oxo-4H-1H-benzopyran

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.14 g 2-carboethoxy-5-hydroxy-3-(4-methoxyphenyl)-7-(4-(quinolin-2-ylmethoxy)benzyloxy)-4-oxo-4H-1-benzopyran and 0.78 g sodium bicarbonate are combined in 7 ml of water and 7 ml of ethanol and refluxed overnight. The mixture is extracted with ether and the aqueous neutralized to pH6. The resulting solid is collected, dried to give 2-carboxy-5-hydroxy-3-(4-methoxyphenyl)7-(4-(quinolin-2-ylmethoxy)benzyloxy)-4-oxo-4H-1H-benzopyran; m.p. 195°-96° C.

Workup

  1. extractionThe mixture is extracted with ether
  2. customThe resulting solid is collected
  3. customdried

Sources & evidence

ORD record
ord-fe8a277088fa41629ed571839e545d18
Source dataset
uspto-grants-1990_12
Patent number
US04977162

Reaction notes

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