Ethanolamine → HCID 11415597, compound

HRID 639880Notes

Reaction equation

HRID 639880 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[C:5]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:4]([CH3:20])[N:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH2:27]([CH2:29][NH2:30])[OH:28]>>[CH3:13][O:12][C:8]1[CH:7]=[C:6]2[C:11](=[CH:10][CH:9]=1)[C:2]([NH:30][CH2:29][CH2:27][OH:28])=[N:3][C:4]([CH3:20])=[C:5]2[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 3

HCID 700EthanolamineHCID 10340Sodium CarbonateHCID 86041352HCID 86041352, compound

Product 1

HCID 11415597HCID 11415597, compound

Procedure

1-chloro-6-methoxy-3-methyl-4-phenylisoquinoline (0.29 g) was combined with 10 mL of ethanolamine and heated at 120 C for 5 h, then cooled to room temp. The reaction was poured into saturated aqueous sodium carbonate and extracted with EtOAc (3×). The combined organic solutions were washed with water (1×), then dried (Na2SO4) and concentrated. Flash chromatography (10% MeOH/CHCl2) gave a solid which was recrystallized from ether/hexanes to give the titled compound.

Workup

  1. temperatureheated at 120 C for 5 h
  2. extractionextracted with EtOAc (3×)
  3. washThe combined organic solutions were washed with water (1×)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customFlash chromatography (10% MeOH/CHCl2) gave a solid which
  7. customwas recrystallized from ether/hexanes

Sources & evidence

ORD record
ord-5415c9ae92e24eac8bef56727dc42fc2
Source dataset
uspto-grants-2010_04
Patent number
US07691879B2

Reaction notes

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