4-Aminophenol → 4-(4-(4-Methoxyphenyl)phthalazin-1-ylamino)phenol hydrochloride

HRID 1042793Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[Cl:9][C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)=[N:12][N:11]=1.C(O)(CC)C>C(OCC)C>[ClH:9].[CH3:27][O:26][C:23]1[CH:22]=[CH:21][C:20]([C:13]2[C:14]3[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:10]([NH:1][C:2]3[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=3)=[N:11][N:12]=2)=[CH:25][CH:24]=1

Participants

Conditions

Temperature: 100 °C

Procedure

4-Aminophenol (340 mg, 3.1 mmol), 1-chloro-4-(4-methoxyphenyl)phthalazine (837 mg, 3.1 mmol), and sec-butanol (12 mL, 3.1 mmol) were combined in a resealable tube and heated to 100° C. overnight. The reaction progress was monitored by LCMS, and upon completion, the orange reaction was cooled diluted with diethyl ether. The resulting precipitate was filtered and washed with diethyl ether, and the solid was dried in vacuo to provide 4-(4-(4-methoxyphenyl)phthalazin-1-ylamino)phenol hydrochloride (1.17 g, 100% yield) as an orange solid. MS [M+H]=344.0. Calc'd for C19H21N5O: 343.13.

Workup

customupon completion, the orange reaction
temperaturewas cooled
filtrationThe resulting precipitate was filtered
washwashed with diethyl ether
customthe solid was dried in vacuo

Sources & evidence

ORD record: ord-b081803c459848febde67b5f8b3f667b
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08557816B2

Reaction notes

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