Nitric Acid → HCID 66759560, compound

HRID 1402792Notes

Reaction equation

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

Participants

Conditions

Temperature: 30 °C

Procedure

N-(4-Phenoxyphenyl)-3-(4-chlorophenyl)glutaramic acid (1.41 g) was dissolved in acetic acid (3 ml) with heating. The solution was allowed to cool to 30° C. With vigorous stirring fuming nitric acid (0.7 ml) was rapidly added in portions. The resulting hot, orange coloured solution was stirred at rt for 0.5 h. With ice cooling water (15 ml) was added slowly. From the gummy, yellow precipitate the aqueous layer is removed by decantation. Crystallisation is induced by heating with methanol (4 ml). After cooling to rt the precipitate is isolated by filtration, washed with methanol, and dried in vacuo to yield bright yellow crystals (1.21 g) of N-(2-nitro-4-phenoxyphenyl)-3-(4-chlorophenyl)glutaramic acid.

Workup

temperaturewith heating
additionwas added slowly
customFrom the gummy, yellow precipitate the aqueous layer is removed by decantation
customCrystallisation
temperatureby heating with methanol (4 ml)
temperatureAfter cooling to rt the precipitate
customis isolated by filtration
washwashed with methanol
customdried in vacuo

Sources & evidence

ORD record: ord-e47eecf253074fe2a65823fe10603515
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08912186B2

Reaction notes

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