Ethanol → HCID 20183514, compound

HRID 255503Notes

Reaction equation

HRID 255503 reaction equation
[C:1]1([CH2:7][N:8]2[C:17]3[C:12](=[CH:13][C:14]4CC=[C:22]([C:25]([O:27]CC)=[O:26])[O:21][C:15]=4[C:16]=3[CH2:18][CH2:19][CH3:20])[CH2:11][CH:10]=[CH:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:30]([OH:32])[CH3:31].[OH-:33].[Na+]>>[O:32]=[C:30]1[C:14]2[CH:13]=[C:12]3[C:17](=[C:16]([CH2:18][CH2:19][CH3:20])[C:15]=2[O:21][C:22]([C:25]([OH:27])=[O:26])=[CH:31]1)[N:8]([CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[CH:9]=[CH:10][C:11]3=[O:33]

Participants

4

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 20183524HCID 20183524, compound

Product 1

HCID 20183514HCID 20183514, compoundYield 32%

Procedure

A suspension of ethyl 6,9-dihydro-9-phenylmethyl-10-propyl-4H-pyrano[3,2-g]quinoline-2-carboxylate (1.8 g, 4.6 mmol) in 0.1 N aqueous sodium hydroxide solution (46.9 ml) containing ethanol (10 ml) was heated at reflux for 6 hours. The mixture was cooled, filtered and the filtrate was acidified and filtered. The solid obtained was dried (in vacuo) at 80° to give the required acid as a yellow powder 0.6 g (32%) mp>250°.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 6 hours
  3. temperatureThe mixture was cooled
  4. filtrationfiltered
  5. filtrationfiltered
  6. customThe solid obtained
  7. customwas dried (in vacuo) at 80°

Sources & evidence

ORD record
ord-76291c578a57418b97786cb3f679c89d
Source dataset
uspto-grants-1987_10
Patent number
US04698345

Reaction notes

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