Sodium Hydroxide → HCID 20366318, compound

HRID 616847Notes

Reaction equation

HRID 616847 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH:9]=[C:8]([NH:11][C:12](=[O:18])[C:13]([O:15]CC)=[O:14])[C:7](=[O:19])[C:6]=2[CH:20]=1.[OH-].[Na+]>C(O)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH:9]=[C:8]([NH:11][C:12](=[O:18])[C:13]([OH:15])=[O:14])[C:7](=[O:19])[C:6]=2[CH:20]=1

Participants

5

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 53717011HCID 53717011, compound

Product 1

HCID 20366318HCID 20366318, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Ethyl (6-chloro-4-oxo-4H-1-benzopyran-3-yl)aminooxoacetate (2.7g, 0.92 mole) was suspended in ethanol (100 ml) and water (100 ml). 0.1N sodium hydroxide solution was added dropwise, with occasional warming on a steam bath, until the reaction mixture remained slightly basic. The color of the mixture changed to orange on addition of the base and then back to white. The sodium hydroxide solution was added until a faint orange color persisted. The product was filtered off, triturated with 1N hydrochloric acid, washed with water and sucked dry on filter. Recrystallization from methanol gave white crystals (2,3g, 94%), m.p. 213°-215° C.

Workup

  1. temperaturewith occasional warming on a steam bath, until the reaction mixture
  2. additionorange on addition of the base
  3. filtrationThe product was filtered off
  4. customtriturated with 1N hydrochloric acid
  5. washwashed with water
  6. customsucked dry
  7. filtrationon filter
  8. customRecrystallization from methanol
  9. customgave white crystals (2,3g, 94%), m.p. 213°-215° C.

Sources & evidence

ORD record
ord-0c3cceb682ac4d0ebed40db3e0b9365a
Source dataset
uspto-grants-1978_02
Patent number
US04076729

Reaction notes

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