HCID 23072936, compound → HCID 23072935, compound

HRID 552599Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:24]=[C:25]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:26]=1)[C:12]([NH:14][C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][N:16]=1)=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CN(C=O)C.O.[Zn]>[CH2:28]([O:27][C:25]1[CH:24]=[C:11]([CH:10]=[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:26]=1)[C:12]([NH:14][C:15]1[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][N:16]=1)=[O:13])[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To a stirred solution of 2-[(3,5-dibenzyloxybenzoyl)amino]-5-nitropyridine (910 mg) in DMF (6 ml) was added Zinc dust (1300 mg) and a solution of ferric chloride hexahydrate (1700 mg) in water (6 ml). The resulting mixture was stirred at 120° C. for three hours. Allowed to cool to ambient temperature. The mixture was extracted with ethyl acetate. The extract was washed with water (50 ml), brine (50 ml), dried over MgSO4, then volatile material was removed by evaporation to leave a solid, which was dried under high vacuum for 24 hours at 100° C. to give the title compound (518 mg) as a solid, 1H NMR δ (d6-DMSO): 5.17 (m, 6H), 6.80 (s, 1H), 7.00 (d, 1H), 7.26 to 7.46 (m, 12H), 7.71 (s, 1H), 7.78 (d, 1H), 10.28 (br s, 1H). MS ES+ 426.52 (M+H)+.

Workup

temperatureAllowed to cool to ambient temperature
extractionThe mixture was extracted with ethyl acetate
washThe extract was washed with water (50 ml), brine (50 ml)
dry with materialdried over MgSO4
customvolatile material was removed by evaporation
customto leave a solid, which
customwas dried under high vacuum for 24 hours at 100° C.

Sources & evidence

ORD record: ord-9117d8ebda1848fc980c4f134842d6a6
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07951830B2

Reaction notes

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