Sodium Hydroxide → 7-Diethylaminocoumarin-3-carboxylic acid

HRID 443319Notes

Reaction equation

HRID 443319 reaction equation
[CH2:1]([N:3]([CH2:20][CH3:21])[C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[C:9]([C:15]([O:17]CC)=[O:16])[C:10](=[O:14])[O:11]2)=[CH:6][CH:5]=1)[CH3:2].[OH-].[Na+]>CO>[CH2:20]([N:3]([CH2:1][CH3:2])[C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[C:9]([C:15]([OH:17])=[O:16])[C:10](=[O:14])[O:11]2)=[CH:6][CH:5]=1)[CH3:21]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 1200142H-1-Benzopyran-3-carboxylic acid, 7-(diethylamino)-2-oxo-, ethyl ester

Product 1

HCID 6592947-Diethylaminocoumarin-3-carboxylic acidYield 89.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

--A solution of the ester 1 (11.6g, 40 mmol) in MeOH (100 ml) was heated under reflux and 0.5 M aq. NaOH (100 ml) was added rapidly. A yellow solid precipitated within 5 min and the mixture was cooled and acidified with 2 M aq. HCl to give an orange solid which was filtered and washed with 2 M aq. HCl, then with water until neutral and finally with MeOH (50 ml), and dried in vacuo to give the acid 2 (9.4 g) A sample recrystallised from MeOH-diisopropyl ether as orange laths, m.p. 231-232° C. (lit. m.p. 227-229° C. see U.S. Pat. No. 4,317,774).

Workup

  1. temperatureunder reflux
  2. customA yellow solid precipitated within 5 min
  3. temperaturethe mixture was cooled
  4. customto give an orange solid which
  5. filtrationwas filtered
  6. washwashed with 2 M aq. HCl
  7. dry with materialwith water until neutral and finally with MeOH (50 ml), and dried in vacuo

Sources & evidence

ORD record
ord-1191c5e243d24bbe82fbf462e40eee1b
Source dataset
uspto-grants-1999_04
Patent number
US05898069

Reaction notes

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