Ammonia → 1H-Imidazo[4,5-c]quinoline-2,4-diamine, 1-(2-methylpropyl)-

HRID 1097550Notes

Reaction equation

Br.Cl[C:3]1[C:12]2[N:13]=[C:14]([NH2:20])[N:15]([CH2:16][CH:17]([CH3:19])[CH3:18])[C:11]=2[C:10]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[N:4]=1.[NH3:21]>CO>[CH3:18][CH:17]([CH3:19])[CH2:16][N:15]1[C:11]2[C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:4]=[C:3]([NH2:21])[C:12]=2[N:13]=[C:14]1[NH2:20]

Participants

Conditions

Temperature: 150 °C

Procedure

4-Chloro-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline-2-amine hydrobromide (8.61 g) and ammonia (131 mL of a 7 N solution in methanol) were added to a high-pressure vessel, which was sealed and heated overnight in an oven at 150° C. The resulting solution was concentrated under reduced pressure to provide 7 g of crude product. A portion of the product was purified by flash chromatography on silica gel (eluting with 3-4% methanol in dichloromethane with 1% ammonium hydroxide added.) The isolated product was washed with methanol, purified again by flash chromatography using the same conditions, and dried under high vacuum to provide 1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline-2,4-diamine as a gray, crystalline solid, mp >250° C. Anal. calcd. for C14H17N5: C, 65.68; H, 6.71; N, 27.43. Found: C, 65.69; H, 6.79; N, 27.42.

Workup

customwhich was sealed
concentrationThe resulting solution was concentrated under reduced pressure
customto provide 7 g of crude product
customA portion of the product was purified by flash chromatography on silica gel (eluting with 3-4% methanol in dichloromethane with 1% ammonium hydroxide added.) The isolated product
washwas washed with methanol
custompurified again by flash chromatography
customdried under high vacuum

Sources & evidence

ORD record: ord-98613331d8a84f2988c066e00285624c
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08143270B2

Reaction notes

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