Hydrogen Bromide → HCID 21402603, compound

HRID 1606330Notes

Reaction equation

HRID 1606330 reaction equation
[CH2:1]([C:4]1[CH:5]=[C:6]([CH2:18][CH2:19][CH3:20])[C:7]2[O:12][C:11]([C:13](N)=[O:14])=[CH:10][C:9](=[O:16])[C:8]=2[CH:17]=1)[CH2:2][CH3:3].Br.[OH2:22]>C(O)(=O)C>[CH2:1]([C:4]1[CH:5]=[C:6]([CH2:18][CH2:19][CH3:20])[C:7]2[O:12][C:11]([C:13]([OH:22])=[O:14])=[CH:10][C:9](=[O:16])[C:8]=2[CH:17]=1)[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 962WaterHCID 21402618HCID 21402618, compound

Product 1

HCID 21402603HCID 21402603, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A mixture of 1.0 parts of 6,8-dipropyl-4-oxo-4H-1-benzopyran-2-carboxamide, 20 parts of glacial acetic acid, and 20 parts of a solution of hydrogen bromide (45% weight/volume) in glacial acetic acid was heated at reflux for 3 hours, then added to water and extracted with chloroform. Extraction of the organic layer with saturated sodium bicarbonate solution, followed by acidification of the bicarbonate layer, afforded 0.16 parts of 6,8-dipropyl-4-oxo-4H-1-benzopyran-2-carboxylic acid, melting point 183°-184°C (decomposition). The melting point, IR spectrum and thin layer chromatographic properties of this material were identical with those of the compound prepared in Example 8.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 hours
  3. extractionextracted with chloroform
  4. extractionExtraction of the organic layer with saturated sodium bicarbonate solution

Sources & evidence

ORD record
ord-ed1f59c156ab480d85da49576f5e355c
Source dataset
uspto-grants-1976_04
Patent number
US03952104

Reaction notes

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