Ammonium Hydroxide → 2H-1-Benzopyran-6-carboxylic acid, 3-(1H-imidazol-1-ylmethyl)-

HRID 1590664Notes

Reaction equation

HRID 1590664 reaction equation
[N:1]1([CH2:6][CH:7]2[CH:12](O)[C:11]3[CH:14]=[C:15]([C:18]([OH:20])=[O:19])[CH:16]=[CH:17][C:10]=3[O:9][CH2:8]2)[CH:5]=[CH:4][N:3]=[CH:2]1.[OH-].[NH4+]>C(O)(=O)C.S(=O)(=O)(O)O>[N:1]1([CH2:6][C:7]2[CH2:8][O:9][C:10]3[CH:17]=[CH:16][C:15]([C:18]([OH:20])=[O:19])=[CH:14][C:11]=3[CH:12]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

5

Reactant 2

HCID 14923Ammonium HydroxideHCID 15049014HCID 15049014, compound

Product 1

HCID 30759782H-1-Benzopyran-6-carboxylic acid, 3-(1H-imidazol-1-ylmethyl)-Yield 53.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1118Sulfuric AcidSolvent

Procedure

A solution of 3,4-dihydro-3(1H-imidazol-1-ylmethyl)-4-hydroxy-2H-1-benzopyran-6-carboxylic acid (3.0 g) in glacial acetic acid (60 ml) and concentrated sulfuric acid (30 ml) is heated at 80° C. for 3 hours. After cooling, the reaction mixture is poured into crushed ice, neutralized with ammonium hydroxide and extracted with methylene chloride. The organic layer is dried over sodium sulfate and evaporated to dryness. The resulting residue is treated with ethyl ether to give 1.5 g of 3-(1H-imidazol-1-ylmethyl)-2H-1-benzopyran-6-carboxylic acid, m.p. 258°-259°.

Workup

  1. temperatureAfter cooling
  2. additionthe reaction mixture is poured
  3. custominto crushed ice
  4. extractionextracted with methylene chloride
  5. dry with materialThe organic layer is dried over sodium sulfate
  6. customevaporated to dryness
  7. additionThe resulting residue is treated with ethyl ether

Sources & evidence

ORD record
ord-42426a47a64b4753bbc732ec0385c44a
Source dataset
uspto-grants-1993_04
Patent number
US05204364

Reaction notes

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