2-(Methylamino)ethanol → HCID 131718854, compound

HRID 274374Notes

Reaction equation

HRID 274374 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

4

Reactant 2

HCID 80162-(Methylamino)ethanolHCID 69878366HCID 69878366, compound

Product 1

HCID 131718854HCID 131718854, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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.

Workup

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

Sources & evidence

ORD record
ord-fe6239f7881640f7b65c198c3a6dcf4d
Source dataset
uspto-grants-1995_02
Patent number
US05389640

Reaction notes

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