Ethyl orthoformate → HCID 69666208, compound

HRID 1839104Notes

Reaction equation

HRID 1839104 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[NH:12][C@H:13]([CH2:16][CH3:17])[CH2:14][OH:15])=[CH:9][CH:8]=[CH:7][CH:6]=2.[CH2:18](OC(OCC)OCC)C>>[N:12]1([C@H:13]([CH2:16][CH3:17])[CH2:14][OH:15])[C:11]2[C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:4]=[CH:3][C:2]=2[N:1]=[CH:18]1

Participants

3

Reactant 2

HCID 31214Ethyl orthoformateHCID 69666132HCID 69666132, compound

Product 1

HCID 69666208HCID 69666208, compound

Conditions

Temperature
145 °C

Procedure

(2R)-2-[(3-Aminoquinolin-4-yl)amino]butan-1-ol (416.0 g, 1 eq.) and triethylorthoformate (1.2 L, 4 eq.) were combined and slowly heated to 145° C. Ethanol was distilled off as it formed during the reaction. After ˜500 mL of ethanol had been distilled off, the reaction mixture was allowed to cool to 50° C. under a nitrogen atmosphere. Excess triethyLorthoformate was removed under reduced pressure to provide crude (2R)-2-(1H-imidazo[4,5-c]quinolin-1-yl)butan-1-ol.

Workup

  1. distillationEthanol was distilled off as it
  2. customformed during the reaction
  3. distillationAfter ˜500 mL of ethanol had been distilled off
  4. temperatureto cool to 50° C. under a nitrogen atmosphere
  5. customExcess triethyLorthoformate was removed under reduced pressure

Sources & evidence

ORD record
ord-1fc1d521b506491386a37b77971c8d4a
Source dataset
uspto-grants-2004_01
Patent number
US06677348B2

Reaction notes

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