Oxalic Acid → 8,9-dihydro-7-[(hydroxy)(2-methylpyridin-3-yl)methyl]-10-methylpyrido[1,2-a]indol-6(7H)-one

HRID 486197Notes

Reaction equation

HRID 486197 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.[CH3:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]2[C:23](=[O:27])[CH2:24][CH2:25][CH2:26][C:15]=12.[CH3:28][C:29]1[C:34]([CH:35]=[O:36])=[CH:33][CH:32]=[CH:31][N:30]=1.C(O)(=O)C(O)=O>O1CCCC1.CCCCCC.O>[OH:36][CH:35]([C:34]1[C:29]([CH3:28])=[N:30][CH:31]=[CH:32][CH:33]=1)[CH:24]1[C:23](=[O:27])[N:16]2[C:17]3[C:22]([C:14]([CH3:13])=[C:15]2[CH2:26][CH2:25]1)=[CH:21][CH:20]=[CH:19][CH:18]=3

Participants

9

Reactant 5

HCID 971Oxalic AcidHCID 7912DiisopropylamineHCID 1107438710-methyl-8,9-dihydropyrido[1,2-a]indol-6(7H)-oneHCID 110838812-Methylpyridine-3-carbaldehydeHCID 178418339Butyllithium

Product 1

HCID 103361388,9-dihydro-7-[(hydroxy)(2-methylpyridin-3-yl)methyl]-10-methylpyrido[1,2-a]indol-6(7H)-one

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×HCID 8058HexaneSolvent

Procedure

To a solution of diisopropylamine (1.01 g) in tetrahydrofuran (15 ml) at -70° C. under a nitrogen atmosphere was added 1.64M butyllithium in hexane (6.1 ml). After being stirred at the same temperature for 20 minutes, the mixture was treated with a solution of 8,9-dihydro-10-methylpyrido[1,2-a]indol-6(7H)-one (1.99 g) in tetrahydrofuran (25 ml) over 20 minutes. The mixture was stirred at -70° C. for 30 minutes, and a solution of 2-methyl-3-pyridinecarbaldehyde (1.21 g) in tetrahydrofuran (20 ml) was added dropwise over 20 minutes. After the mixture was stirred at -70° C. for further 60 minutes and at ambient temperature for 60 minutes, it was diluted with water and adjusted to pH 9 with oxalic acid. The separated organic layer was washed with brine, dried over anhydrous magnesium sulfate, and evaporated in vacuo, to give 8,9-dihydro-7-[(hydroxy)(2-methylpyridin- 3-yl)methyl]-10-methylpyrido[1,2-a]indol-6(7H)-one.

Workup

  1. stirringThe mixture was stirred at -70° C. for 30 minutes
  2. stirringAfter the mixture was stirred at -70° C. for further 60 minutes and at ambient temperature for 60 minutes
  3. washThe separated organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-ad2d57dfa9734abba596b1206b345d3f
Source dataset
uspto-grants-1994_03
Patent number
US05290785

Reaction notes

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