2-(Methylamino)ethanol → HCID 131718854, compound

HRID 396963Notes

Reaction equation

Cl.Cl[CH2:3][C:4]1[N:5]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:6]2[C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N:9]=[C:8]([NH2:16])[C:7]=2[N:17]=1.[CH3:25][NH:26][CH2:27][CH2:28][OH:29]>O>[OH2:29].[NH2:16][C:8]1[C:7]2[N:17]=[C:4]([CH2:3][N:26]([CH2:27][CH2:28][OH:29])[CH3:25])[N:5]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:6]=2[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N:9]=1.[NH2:16][C:8]1[C:7]2[N:17]=[C:4]([CH2:3][N:26]([CH3:25])[CH2:27][CH2:28][OH:29])[N:5]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:6]=2[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N:9]=1

Participants

Conditions

Temperature: 130 °C

Procedure

2-Chloromethyl-1-phenylmethyl-1H-imidazo-[4,5-c]quinolin-4-amine hydrochloride (Example 28, prepared from 1.4 g of the alcohol) was added to N-methylethanolamine (20 mL). The mixture was heated in an oil bath for 3 hr at about 130° C. The solution was diluted with water and the mixture extracted with diethyl ether (7×200 mL). The combined extracts were washed with saturated sodium chloride solution and evaporated to dryness to yield an orange solid. The crude product was recrystallized from methanol/dichloromethane. m.p. 188-195° C. Analysis: Calculated: C, 68.1; H, 6.5; N, 18.9. Found: C, 68.4; H, 6.5: N, 18.7.

Workup

extractionthe mixture extracted with diethyl ether (7×200 mL)
washThe combined extracts were washed with saturated sodium chloride solution
customevaporated to dryness
customto yield an orange solid
customThe crude product was recrystallized from methanol/dichloromethane

Sources & evidence

ORD record: ord-85f42de285b1492e8e8136fb229c988f
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06608201B2

Reaction notes

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