Ethanol → HCID 14822501, compound

HRID 2073785Notes

Reaction equation

HRID 2073785 reaction equation
CO[C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]1[N:13]([CH3:18])[N:14]=[C:15]([C:16]#[N:17])[C:7]1=[CH:6]2.[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:25]([OH:27])C>O1CCCC1.C1(C)C=CC=CC=1.[Pd]>[CH3:25][O:27][C:12]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]3[C:15]([CH2:16][NH2:17])=[N:14][N:13]([CH3:18])[C:8]3=[N:9]2)=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 702EthanolHCID 14822500HCID 14822500, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 14822501HCID 14822501, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 8.6 g 6-methoxy-1-methyl-1H-pyrazolo[3,4-b]quinoline-3-carbonitrile (Example 33) and 3.8 g lithium aluminum hydride in 500 ml tetrahydrofuran was stirred at room temperature for about sixteen hours. The crude product was isolated and dissolved in 200 ml toluene. Ethanol (10 ml) and 2 g palladium-on-carbon catalyst (10%) was added, and the mixture was heated to reflux and stirred for about sixteen hours. The reaction mixture was filtered and concentrated, and the residue was chromatographed and crystallized from ethanol to give 2.9 g 7-methoxy-1-methyl-1H-pyrazolo[3,4-b]quinoline-3-methanamine, brownish-yellow solid, m.p. 119°-120° C.

Workup

  1. customThe crude product was isolated
  2. temperaturethe mixture was heated
  3. temperatureto reflux
  4. stirringstirred for about sixteen hours
  5. filtrationThe reaction mixture was filtered
  6. concentrationconcentrated
  7. customthe residue was chromatographed
  8. customcrystallized from ethanol

Sources & evidence

ORD record
ord-9c0e720fe49940319c51499ed2be0ee3
Source dataset
uspto-grants-1990_04
Patent number
US04920128

Reaction notes

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