2-Aminophenol → HCID 57441062, compound

HRID 2391558Notes

Reaction equation

Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[CH:9][N:10]=2)[N:7]=1.[NH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[OH:18].C(=O)([O-])[O-].[K+].[K+].CN1CCCC1=O>[OH-].[Na+]>[N:10]1[CH:9]=[CH:8][N:6]2[C:5]=1[CH:4]=[CH:3][C:2]([O:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[NH2:11])=[N:7]2

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 6-chloroimidazo[1,2-b]pyridazine (1536 mg, 10.0 mmol), 2-aminophenol (1419 mg, 13.0 mmol), potassium carbonate (4146 mg, 30.0 mmol) and N-methylpyrrolidone (10 mL) was stirred at 120° C. for 3 days. The reaction mixture was diluted with 1N aqueous sodium hydroxide solution and extracted with ethyl acetate. The organic layer was concentrated under reduced pressure, and the residue was purified by NH silica gel column chromatography (hexane/ethyl acetate=70/30→0/100). The objective fraction was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/methanol=100/0→75/25), and precipitated from diisopropyl ether to give the title compound (307 mg, 1.4 mmol, yield 14%) as a pale-brown solid.

Workup

extractionextracted with ethyl acetate
concentrationThe organic layer was concentrated under reduced pressure
customthe residue was purified by NH silica gel column chromatography (hexane/ethyl acetate=70/30→0/100)
concentrationThe objective fraction was concentrated under reduced pressure
customthe residue was purified by silica gel column chromatography (ethyl acetate/methanol=100/0→75/25)
customprecipitated from diisopropyl ether

Sources & evidence

ORD record: ord-a6cc52d4c82746a8ad494c02370057a4
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08273741B2

Reaction notes

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