Sodium Bicarbonate → 2-carboxy-8-(4-(quinolin-2-ylmethoxy)phenoxymethyl)-4-oxo-4H-1-benzopyran

HRID 1110906Notes

Reaction equation

HRID 1110906 reaction equation
[C:1]([C:6]1[O:7][C:8]2[C:16]([CH2:17][O:18][C:19]3[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]4[CH:36]=[CH:35][C:34]5[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=5)[N:28]=4)=[CH:21][CH:20]=3)=[CH:15][CH:14]=[CH:13][C:9]=2[C:10](=[O:12])[CH:11]=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[C:16]([CH2:17][O:18][C:19]3[CH:20]=[CH:21][C:22]([O:25][CH2:26][C:27]4[CH:36]=[CH:35][C:34]5[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=5)[N:28]=4)=[CH:23][CH:24]=3)=[CH:15][CH:14]=[CH:13][C:9]=2[C:10](=[O:12])[CH:11]=1)([OH:3])=[O:2]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 19913843HCID 19913843, compound

Product 1

HCID 148423732-carboxy-8-(4-(quinolin-2-ylmethoxy)phenoxymethyl)-4-oxo-4H-1-benzopyranYield 61.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

0.74 g of 2-carboethoxy-8-(4-(quinoline-2-ylmethoxy)phenoxymethyl)-4-oxo-4H-1-benzopyran 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 0.43 g 2-carboxy-8-(4-(quinolin-2-ylmethoxy)phenoxymethyl)-4-oxo-4H-1-benzopyran; m.p. 221°-24° C.

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-2cd65ca9a2ae4dfc86dfb3379d793d5e
Source dataset
uspto-grants-1990_12
Patent number
US04977162

Reaction notes

Loading…