Ammonium Hydroxide → HCID 9969119, compound

HRID 1635866Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[C:10]([N:12]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[CH2:16][N:15]2[CH:23]=[CH:24][CH:25]=[C:14]2[CH2:13]1)=[O:11])[C:5]#[N:6].[OH-:26].[NH4+]>S(=O)(=O)(O)O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[C:10]([N:12]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[CH2:16][N:15]2[CH:23]=[CH:24][CH:25]=[C:14]2[CH2:13]1)=[O:11])[C:5]([NH2:6])=[O:26]

Participants

Conditions

Temperature: 60 °C

Procedure

Concentrated sulfuric acid (70 ml) was added to 3-chloro-4-(5H,11H-pyrrolo-[2,1-c][1,4]benzodiazepine-10-carbonyl)-benzonitrile (12.85 g). The mixture was stirred at 60° C. for 3 hours, followed by stirring at room temperature for 18 hours. The reaction mixture was poured over ice and neutralized at 0° C., with 30% ammonium hydroxide (184 ml). The resulting suspension was extracted with ethyl acetate. The aqueous mixture was filtered, and reextracted with ethyl acetate. The combined organic phase was dried over anhydrous sodium sulfate, and the solvent removed in vacuo. The residue was triturated with a mixture of diethyl ether (50-60 ml) and a small quantity of ethyl acetate. Filtration of the precipitate afforded the title compound as a crystalline solid (10.44 g), m.p. 211-212° C.; MS (EI), m/z: 365 (M)+.

Workup

stirringby stirring at room temperature for 18 hours
extractionThe resulting suspension was extracted with ethyl acetate
filtrationThe aqueous mixture was filtered
dry with materialThe combined organic phase was dried over anhydrous sodium sulfate
customthe solvent removed in vacuo
customThe residue was triturated with a mixture of diethyl ether (50-60 ml)
filtrationFiltration of the precipitate

Sources & evidence

ORD record: ord-8fba28badfbe47719cd2ae57089ef1ee
Source dataset: uspto-grants-2003_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06511974B1

Reaction notes

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