7-Benzyloxy-2-methyl-4-pyrrolidin-1-yl-quinoline → 2-Methyl-4-pyrrolidin-1-yl-quinolin-7-ol

HRID 2415464Notes

Reaction equation

HRID 2415464 reaction equation
C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([N:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)=[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]([N:20]2[CH2:24][CH2:23][CH2:22][CH2:21]2)[C:12]2[C:17](=[CH:18][C:9]([OH:8])=[CH:10][CH:11]=2)[N:16]=1

Participants

4

Reactant 1

HCID 226413107-Benzyloxy-2-methyl-4-pyrrolidin-1-yl-quinoline

Product 1

HCID 1358041182-Methyl-4-pyrrolidin-1-yl-quinolin-7-olYield 96.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 13 g of 7-benzyloxy-2-methyl-4-pyrrolidin-1-yl-quinoline, product of example 1, dissolved in 750 ml of MeOH was treated with 4 g of palladium on charcoal (10%) and then hydrogenated at RT for 1.5 h until HPLC analysis indicated the completion of the reaction. The catalyst was filtered off, washed with water) and the solution was concentrated in vacuo. The solid that precipitated was collected by filtration and dried in a high vacuum to give 8.9 g (96.2%) of 2-methyl-4-pyrrolidin-1-yl-quinolin-7-ol as an amorphous yellow solid. ISP mass spectrum, m/e: 229.2 (M+1 calculated for C14H16N2O: 229).

Workup

  1. customthe completion of the reaction
  2. filtrationThe catalyst was filtered off
  3. washwashed with water) and the solution
  4. concentrationwas concentrated in vacuo
  5. customThe solid that precipitated
  6. filtrationwas collected by filtration
  7. customdried in a high vacuum

Sources & evidence

ORD record
ord-f2f2c1a93a9549eabd0225aceb952929
Source dataset
uspto-grants-2004_11
Patent number
US06818767B2

Reaction notes

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