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

HRID 1951297Notes

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: Found 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-754ac9ae0c244880aa6dd0d9c51ebb31
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08404694B2

Reaction notes

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