Diisobutylaluminum hydride → 1-Benzyl-5-chloro-3-hydroxymethylcinnolin-4(1H)-one

HRID 598156Notes

Reaction equation

HRID 598156 reaction equation
[CH2:1]([N:8]1[C:17]2[C:12](=[C:13]([Cl:18])[CH:14]=[CH:15][CH:16]=2)[C:11](=[O:19])[C:10]([C:20](OC)=[O:21])=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C[AlH]CC(C)C)C>O1CCCC1>[CH2:1]([N:8]1[C:17]2[C:12](=[C:13]([Cl:18])[CH:14]=[CH:15][CH:16]=2)[C:11](=[O:19])[C:10]([CH2:20][OH:21])=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 67266995Methyl 1-benzyl-5-chloro-4-oxo-1,4-dihydrocinnoline-3-carboxylate

Product 1

HCID 672672091-Benzyl-5-chloro-3-hydroxymethylcinnolin-4(1H)-oneYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 0.80 g (2.4 mmol) of methyl 1-benzyl-5-chloro-4-oxo-1,4-dihydrocinnoline-3-carboxylate in 50 mL of tetrahydrofuran at −78° C. was added 7.3 mL (7.3 mmol) of DIBAL (1M in tetrahydrofuran). The mixture was allowed to warm to room temperature and stirred for 6 h. The reaction was quenched with 1N HCl and concentrated to a slurry. The slurry was dissolved in dichloromethane and was concentrated onto silica gel. The crude material was purified by flash chromatography eluting with a 4% methanol/dichloromethane mixture to give 0.44 g (60%) of the title compound as a light yellow powder.

Workup

  1. customThe reaction was quenched with 1N HCl
  2. concentrationconcentrated to a slurry
  3. dissolutionThe slurry was dissolved in dichloromethane
  4. concentrationwas concentrated onto silica gel
  5. customThe crude material was purified by flash chromatography
  6. washeluting with a 4% methanol/dichloromethane mixture

Sources & evidence

ORD record
ord-1e3dbf9531e64d0183b1c3a9f36b6b3b
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Reaction notes

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