Ammonium Hydroxide → HCID 473479, compound

HRID 730079Notes

Reaction equation

HRID 730079 reaction equation
[O:1]=[C:2]1[C:15]2[CH:14]=[CH:13][CH:12]=[C:11]([C:16]([OH:18])=O)[C:10]=2[O:9][C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.C([N:22](C(C)C)CC)(C)C.[OH-].[NH4+]>CN(C)C=O>[O:1]=[C:2]1[C:15]2[CH:14]=[CH:13][CH:12]=[C:11]([C:16]([NH2:22])=[O:18])[C:10]=2[O:9][C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 81531DiisopropylethylamineHCID 410100HCID 410100, compound

Product 1

HCID 473479HCID 473479, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 9-oxo-9H-xanthene-4-carboxylic acid 5j (1.84 g, 7.66 mmol) in dimethylformamide (20 mL) was added N,N-diisopropyl-N-ethylamine (1.74 mmol, 9.96 mmol) and O(benzotriazol-1-yl)-N,N,N′,N′-tetramethyl-uronium hexafluorophosphate (2.9 g, 7.66 mmol). The mixture was stirred for 30 min at rt, and ammonium hydroxide (2 mL) was added. The mixture was stirred for 3 h, poured onto ice, and the solid was collected via filtration. The solid was washed with water and air-dried to yield 1.78 g (97.2% of title compound 6j.

Workup

  1. stirringThe mixture was stirred for 3 h
  2. additionpoured onto ice
  3. filtrationthe solid was collected via filtration
  4. washThe solid was washed with water
  5. customair-dried

Sources & evidence

ORD record
ord-008f6f85b04b45d7a16bba54ac963c28
Source dataset
uspto-grants-2009_09
Patent number
US07582650B2

Reaction notes

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