HCID 178428840, compound → HCID 178428839, compound

HRID 2415503Notes

Reaction equation

HRID 2415503 reaction equation
C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([OH:20])=[CH:14][C:15]([CH3:19])=[N:16]2)=[CH:11][CH:10]=1)C1C=CC=CC=1>CO.[Pd]>[CH3:19][C:15]1[CH:14]=[C:13]([OH:20])[C:12]2[C:17](=[CH:18][C:9]([OH:8])=[CH:10][CH:11]=2)[N:16]=1

Participants

4

Reactant 1

HCID 178428840HCID 178428840, compound

Product 1

HCID 178428839HCID 178428839, compoundYield 111.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 3 g (10.5 mmol) of 7-benzyloxy-2-methyl-quinolin-4-ol, product of example 1 c), dissolved in 270 ml of MeOH was treated with 1 g of palladium on charcoal (10%) and then hydrogenated at RT for 1 h until HPLC analysis indicated the completion of the reaction. The catalyst was filtered off, washed with MeOH, and the solution was concentrated in vacuo. The residue was triturated with ether, collected by filtration and dried in a high vacuum to give 2.05 g (98.6%) 2-methyl-quinoline-4,7-diol as an off-white solid. ISP mass spectrum, m/e: 176.2 (M+1 calculated for C10H9NO2: 176).

Workup

  1. customthe completion of the reaction
  2. filtrationThe catalyst was filtered off
  3. washwashed with MeOH
  4. concentrationthe solution was concentrated in vacuo
  5. customThe residue was triturated with ether
  6. filtrationcollected by filtration
  7. customdried in a high vacuum

Sources & evidence

ORD record
ord-c1c7d703a2f04f74b0c31d78b23fe05f
Source dataset
uspto-grants-2004_11
Patent number
US06818767B2

Reaction notes

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