Sodium Carbonate → Sodium 4-oxo-4H-1-benzopyran-3-carbohydroxamate

HRID 1578608Notes

Reaction equation

HRID 1578608 reaction equation
Cl.[NH2:2][OH:3].C(=O)([O-])[O-].[Na+:8].[Na+].[O:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13](=[O:20])[C:12]([C:21](Cl)=[O:22])=[CH:11]1>O.C(Cl)Cl>[O:20]=[C:13]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=2[O:10][CH:11]=[C:12]1[C:21]([NH:2][O-:3])=[O:22].[Na+:8]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 15041156Chromone-3-carbonyl chloride

Product 1

HCID 23720956Sodium 4-oxo-4H-1-benzopyran-3-carbohydroxamate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 8.34 g (0.12 mol) of hydroxylamine hydrochloride in 125 ml of water was mixed with 100 ml of methylenechloride. Solid sodium carbonate (50 g) was added with cooling. With stirring, a solution of 16.5 g (0.079 mol) of chromone-3-carbonylchloride in 250 ml of methylene chloride was added over a period of 5 minutes, keeping the temp. at 15° with ice bath cooling. After 15 minutes reaction time the thick mixture was filtered and washed with 200 ml of ice-water. The damp filter cake was recrystallized from 100 ml of water, wt 1.5 g (8.4%); mp > 300°.

Workup

  1. temperaturewith cooling
  2. temperatureat 15° with ice bath cooling
  3. customAfter 15 minutes reaction time the thick mixture
  4. filtrationwas filtered
  5. washwashed with 200 ml of ice-water
  6. customThe damp filter cake was recrystallized from 100 ml of water, wt 1.5 g (8.4%)

Sources & evidence

ORD record
ord-01953e94ce314b6ea8f68f43aea3d25b
Source dataset
uspto-grants-1976_02
Patent number
US03937837

Reaction notes

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