Diisobutylaluminum hydride → HCID 178519279, compound

HRID 726644Notes

Reaction equation

HRID 726644 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[Cl:12])[N:8]=[C:7]([OH:13])[C:6]([C:14](OC)=[O:15])=[CH:5]2.CC(C[AlH]CC(C)C)C>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[Cl:12])[N:8]=[C:7]([OH:13])[C:6]([CH2:14][OH:15])=[CH:5]2

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 178496926HCID 178496926, compound

Product 1

HCID 178519279HCID 178519279, compoundYield 86.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 6,7-dichloro-2-hydroxyquinoline-3-carboxylate (2.72 g, 10 mmol) was added in small portions to a stirred solution of DIBAL (1M in hexane, 25 ml, 25 mmol) in tetrahydrofuran (25 ml) under nitrogen at 25°-30° C. The mixture was stirred at ambient temperature for 0.5 h and then quenched with an excess of 20% HCl at 5°-10° C. The precipitate was collected and washed with water, tetrahydrofuran and ethyl ether to give 2.12 g of 6,7-dichloro-2-hydroxyquinoline-3-methanol.

Workup

  1. customquenched with an excess of 20% HCl at 5°-10° C
  2. customThe precipitate was collected
  3. washwashed with water, tetrahydrofuran and ethyl ether

Sources & evidence

ORD record
ord-cab3c3d1ec3548dea9ca8aecc6b3be7d
Source dataset
uspto-grants-1998_01
Patent number
US05710139

Reaction notes

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