Ammonium Hydroxide → 4-oxo-4H-chromene-3-carboxamide

HRID 1578610Notes

Reaction equation

HRID 1578610 reaction equation
[O:1]=[C:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[O:5][CH:4]=[C:3]1[C:12](Cl)=[O:13].[OH-].[NH4+:16]>>[O:1]=[C:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[O:5][CH:4]=[C:3]1[C:12]([NH2:16])=[O:13]

Participants

3

Reactant 2

HCID 14923Ammonium HydroxideHCID 15041156Chromone-3-carbonyl chloride

Product 1

HCID 122007774-oxo-4H-chromene-3-carboxamideYield 48.8%

Procedure

A quantity of 0.9 g (0.0043 mol) of 4-oxo-4H-1-benzopyran-3-carbonylchloride was added gradually to a stirred quantity of 15 ml of conc. ammonium hydroxide at room temperature. All solid went into solution when crystals gradually separated. After 15 min. the solid was filtered and washed with water; wt 0.4 g (48.8% yield); mp 220°-225°. Two recrystallizations from 2-propanol gave pure material melting at 250°-252°C.

Workup

  1. customgradually separated
  2. filtrationAfter 15 min. the solid was filtered
  3. washwashed with water
  4. customTwo recrystallizations from 2-propanol

Sources & evidence

ORD record
ord-d71e5d43905d434199b4b5b86dd29cf0
Source dataset
uspto-grants-1976_02
Patent number
US03937837

Reaction notes

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