Ethanolamine → HCID 69522661, compound

HRID 969500Notes

Reaction equation

HRID 969500 reaction equation
[CH3:1][C:2]1[N:25]([CH3:26])[C:5]2[CH:6]=[C:7]([C:20](OCC)=[O:21])[C:8]3[CH2:9][CH2:10][CH:11]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[NH:12][C:13]=3[C:4]=2[N:3]=1.[NH2:27][CH2:28][CH2:29][OH:30]>>[OH:30][CH2:29][CH2:28][NH:27][C:20]([C:7]1[C:8]2[CH2:9][CH2:10][CH:11]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[NH:12][C:13]=2[C:4]2[N:3]=[C:2]([CH3:1])[N:25]([CH3:26])[C:5]=2[CH:6]=1)=[O:21]

Participants

3

Reactant 2

HCID 700EthanolamineHCID 69134270HCID 69134270, compound

Product 1

HCID 69522661HCID 69522661, compoundYield 52%

Conditions

Temperature
145 °C

Procedure

A suspension of 1.0 g (2.9 mmol) ethyl 2,3-dimethyl-8-phenyl-6,7,8,9-tetrahydro-3H-imidazo[4,5h]-quinoline-5-carboxylate in 10 ml 2-aminoethanol was heated to 140-150° C. until no starting material was left. The mixture was partitioned between saturated aqueous ammonium chloride and dichloro-methane/methanol 9:1. The organic layer was separated, dried over anhydrous magnesium sulphate and evaporated. The residue was purified by column chromatography on silica gel (toluene/dioxane/methanol=6:3:1). Crystallization from diisopropyl ether yielded 0.55 g (52%) of the title compound as a colourless solid. m.p. 248-251° C.

Workup

  1. waitwas left
  2. customThe mixture was partitioned between saturated aqueous ammonium chloride and dichloro-methane/methanol 9:1
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous magnesium sulphate
  5. customevaporated
  6. customThe residue was purified by column chromatography on silica gel (toluene/dioxane/methanol=6:3:1)
  7. customCrystallization from diisopropyl ether

Sources & evidence

ORD record
ord-aed018cb1da44da68126150d159b3075
Source dataset
uspto-grants-2007_12
Patent number
US07307084B2

Reaction notes

Loading…