Hydrochloric Acid → N-(2-aminophenyl)-4-(3-cyanopyridin-2-yl)benzamide

HRID 599509Notes

Reaction equation

HRID 599509 reaction equation
C(OC([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16](=[O:31])[C:17]1[CH:22]=[CH:21][C:20]([C:23]2[C:28]([C:29]#[N:30])=[CH:27][CH:26]=[CH:25][N:24]=2)=[CH:19][CH:18]=1)=O)(C)(C)C.Cl>O1CCOCC1>[NH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16](=[O:31])[C:17]1[CH:22]=[CH:21][C:20]([C:23]2[C:28]([C:29]#[N:30])=[CH:27][CH:26]=[CH:25][N:24]=2)=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67269547HCID 67269547, compound

Product 1

HCID 11544171N-(2-aminophenyl)-4-(3-cyanopyridin-2-yl)benzamideYield 82%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

N-(2-t-Butoxycarbonylaminophenyl)-4-(3-cyanopyridin-2-yl)benzamide (210 mg; prepared as described in Method 1 below), 1,4-dioxane (6.8 ml) and a 4M solution of hydrogen chloride in 1,4-dioxane (6.8 ml) were stirred at ambient temperature for 20 hours. The resultant precipitate was collected by filtration and washed with diethyl ether (3×), suspended in water, basified with a 2M aqueous solution of sodium hydroxide and extracted with dichloromethane. The organic extract was dried over sodium sulfate to afford the title compound as a cream solid (130 mg, 82%); NMR Spectrum: (DMSO-d6) 4.94 (br s, 2H), 6.60 (m, 1H), 6.78 (m, 1H), 6.98 (m, 1H), 7.19 (d, 1H), 7.65 (m, 1H), 7.98 (d, 2H), 8.14 (d, 2H), 8.46 (m, 1H), 8.98 (m, 1H), 9.77 (s, 1H); Mass Spectrum: M+H+ 315.

Workup

  1. filtrationThe resultant precipitate was collected by filtration
  2. washwashed with diethyl ether (3×)
  3. extractionextracted with dichloromethane
  4. extractionThe organic extract
  5. dry with materialwas dried over sodium sulfate

Sources & evidence

ORD record
ord-b7b224c3d99d4cc0b280d8577af9ce97
Source dataset
uspto-grants-2011_03
Patent number
US07897778B2

Reaction notes

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