Nitric Acid → 3-Ethoxycarbonyl-6-chloro-7-hydroxy-8-nitro-coumarin

HRID 2195677Notes

Reaction equation

HRID 2195677 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:18])[O:8][C:9]2[C:14]([CH:15]=1)=[CH:13][C:12]([Cl:16])=[C:11]([OH:17])[CH:10]=2)=[O:5])[CH3:2].[N+:19]([O-])([OH:21])=[O:20]>S(=O)(=O)(O)O>[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:18])[O:8][C:9]2[C:14]([CH:15]=1)=[CH:13][C:12]([Cl:16])=[C:11]([OH:17])[C:10]=2[N+:19]([O-:21])=[O:20])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 23085543HCID 23085543, compound

Product 1

HCID 99728893-Ethoxycarbonyl-6-chloro-7-hydroxy-8-nitro-coumarinYield 47.5%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

2.75 g (10.2 mmol) of 3-ethoxycarbonyl-6-chloro-7-hydroxycoumarin was added into 10 ml of concentrated sulfuric acid, 1.74 g (20.4 mmol) of concentrated nitric acid was added in portions under the cooling of ice-salt bath, the reaction was monitored through thin-layer chromatography to confirm the completion, and ice was added to seize the reaction. The reaction mixture was then filtered and washed by water, dried to give 1.52 g of the title compound (241).

Workup

  1. additionwas added in portions under the
  2. temperaturecooling of ice-salt bath
  3. additionwas added
  4. customthe reaction
  5. filtrationThe reaction mixture was then filtered
  6. washwashed by water
  7. customdried

Sources & evidence

ORD record
ord-1b2e0ea8e3644296b343ac5d4a42c651
Source dataset
uspto-grants-2012_12
Patent number
US08338401B2

Reaction notes

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