Water → HCID 10286050, compound

HRID 392185Notes

Reaction equation

HRID 392185 reaction equation
[NH2:1][C:2]1[C:11]([C:12]#[N:13])=[C:10]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O>C1COCC1.C(OCC)(=O)C>[NH2:13][CH2:12][C:11]1[C:2]([NH2:1])=[N:3][C:4]2[C:9]([C:10]=1[C:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

6

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 22663506HCID 22663506, compound

Product 1

HCID 10286050HCID 10286050, compoundYield 11%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

A solution of 2-amino-4-p-tolyl-quinoline-3-carbonitrile (46 mg, 0.177 mmol) in THF (0.5 ml) was added slowly to a suspension of LiAlH4 (67.3 mg, 1.77 mmol) in THF (1 ml) under an atmosphere of argon. The mixture was stirred for 2 h at 40° C. Upon cooling to −20° C., 0.3 ml water added and stirring was continued for 15 min at r.t. The mixture was taken up in ethyl acetate and filtered through dicalite. The filtrate was washed with water and brine, dried (Na2SO4), and evaporated. Purification of the re-dissolved (DMF, 1 ml) residue by automated, preparative HPLC (YMC CombiPrep C18 column 50×20 mm, solvent gradient 5-95% CH3CN in 0.1% TFA(aq) over 6.0 min, λ=230 nm, flow rate 40 ml/min) gave 5 mg (11%) of the title compound as a solid.

Workup

  1. temperatureUpon cooling to −20° C.
  2. stirringstirring
  3. waitwas continued for 15 min at r.t
  4. filtrationfiltered through dicalite
  5. washThe filtrate was washed with water and brine
  6. dry with materialdried (Na2SO4)
  7. customevaporated
  8. customPurification of the
  9. dissolutionre-dissolved (DMF, 1 ml) residue by automated, preparative HPLC (YMC CombiPrep C18 column 50×20 mm, solvent gradient 5-95% CH3CN in 0.1% TFA(aq) over 6.0 min, λ=230 nm, flow rate 40 ml/min)

Sources & evidence

ORD record
ord-ceecd78b77094e1b85379b5ca12d020a
Source dataset
uspto-grants-2004_10
Patent number
US06800650B2

Reaction notes

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