Hydrochloric Acid → Pyridinium, 1-(2-hydroxy-3-(4-(4-nitrobenzoyl)phenoxy)propyl)-4-phenyl-, chloride

HRID 2308987

Reaction equation

[O:1]1[CH2:22][CH:2]1[CH2:3][O:4][C:5]1[CH:21]=[CH:20][C:8]([C:9]([C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=2)=[O:10])=[CH:7][CH:6]=1.[C:23]1([C:29]2[CH:34]=[CH:33][N:32]=[CH:31][CH:30]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[ClH:35]>O1CCOCC1.O>[Cl-:35].[OH:1][CH:2]([CH2:3][O:4][C:5]1[CH:21]=[CH:20][C:8]([C:9](=[O:10])[C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)[CH2:22][N+:32]1[CH:33]=[CH:34][C:29]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:30][CH:31]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A solution of 2.06 g (6.88 mmol) of 4-(2,3-epoxypropoxy)-4'-nitrobenzophenone in 50 ml of dioxan and 25 ml of water was treated with 1.06 g (6.88 mmol) of 4-phenylpyridine and stirred at 70° C. while adding 1N HCl at a pH less than 8. After stirring at 70° C. for 18 hours the mixture was cooled to 20° C., treated with 300 ml of water and extracted three times with 200 ml of chloroform. The organic phase was dried and concentrated. The residue was recrystallized from acetone. There was obtained 1-[2-hydroxy-3-[p-(p-nitrobenzoyl)phenoxy]propyl]-4-phenylpyridinium chloride in 50% yield, m.p. 240° C.

Workup

stirringAfter stirring at 70° C. for 18 hours the mixture
temperaturewas cooled to 20° C.
extractionextracted three times with 200 ml of chloroform
customThe organic phase was dried
concentrationconcentrated
customThe residue was recrystallized from acetone

Sources & evidence

ORD record: ord-283d244cc89b44608f5a42356719d19e
Source dataset: uspto-grants-1987_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04692450

Linked notes

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