Methanol → HCID 23326479, compound

HRID 1380314Notes

Reaction equation

HRID 1380314 reaction equation
B(Br)(Br)Br.C([O:12][CH2:13][CH2:14][N:15]1[C:24]2[C:19](=[CH:20][C:21]([C:25]3[CH:26]([CH3:32])[NH:27][C:28](=[O:31])[NH:29][N:30]=3)=[CH:22][CH:23]=2)[CH2:18][CH2:17][C:16]1=[O:33])C1C=CC=CC=1.CO>C(Cl)Cl>[OH:12][CH2:13][CH2:14][N:15]1[C:24]2[C:19](=[CH:20][C:21]([C:25]3[CH:26]([CH3:32])[NH:27][C:28](=[O:31])[NH:29][N:30]=3)=[CH:22][CH:23]=2)[CH2:18][CH2:17][C:16]1=[O:33]

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 23326443HCID 23326443, compound

Product 1

HCID 23326479HCID 23326479, compoundYield 49.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of boron tribromide (4.59 g) in methylenechloride (5 ml) was added dropwise to a stirred suspension of 6-[1-(2-benzyloxyethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl]-5-methyl-4,5-dihydro-1,2,4-triazin-3(2H)-one (2.38 g) in methylene chloride (200 ml) at -40° C. over a period of 10 minutes. After being stirred for 40 minutes at the same temperature, methanol (0.6 ml) was added to the suspension and evaporated in vacuo. The residue was dissolved in n-butanol, washed with brine, and evaporated in vacuo. The residual solid was washed with ethyl acetate and recrystallized from methanol to give 6-[1-(2-hydroxyethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl]-5-methyl-4,5-dihydro-1,2,4-triazin-3(2H)-one (0.91 g), mp 237° to 243° C.

Workup

  1. additionwas added to the suspension
  2. customevaporated in vacuo
  3. dissolutionThe residue was dissolved in n-butanol
  4. washwashed with brine
  5. customevaporated in vacuo
  6. washThe residual solid was washed with ethyl acetate
  7. customrecrystallized from methanol

Sources & evidence

ORD record
ord-32d1bde77ff5445b8c2512099e12b199
Source dataset
uspto-grants-1986_04
Patent number
US04581356

Reaction notes

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