Sodium Hydroxide → 5,6,7,8-Tetrahydro-3-methyl-7-(phenylmethyl)-2,7-naphthyridine-4-carbonitrile

HRID 1593594Notes

Reaction equation

HRID 1593594 reaction equation
[NH2:1]/[C:2](/[CH3:19])=[C:3](\[C:6]1[CH2:7][CH2:8][N:9]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:10][CH:11]=1)/[C:4]#[N:5].[Cl-].N1(C=[N+](C)C)C2C=CC=C[C:24]=2N=N1.[OH-].[Na+]>ClCCl>[CH2:12]([N:9]1[CH2:8][C:7]2[CH:24]=[N:1][C:2]([CH3:19])=[C:3]([C:4]#[N:5])[C:6]=2[CH2:11][CH2:10]1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 10727199HCID 10727199, compoundHCID 69270089HCID 69270089, compound

Product 1

HCID 589995745,6,7,8-Tetrahydro-3-methyl-7-(phenylmethyl)-2,7-naphthyridine-4-carbonitrileYield 60.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (E)-3-amino-2-(1-benzyl-1,2,3,6-tetrahydro-pyridin-4-yl)-but-2-enenitrile (15 g, 0.056 mole) in dichloromethane (200 mL), freshly prepared benzotriazol-1-ylmethylene-dimethyl-ammonium chloride (12 g, 0.068 mole) was added in one portion. The mixture was stirred for 24 h at ambient temperature. NaOH (2N, 200 mL) was added, and the resulting mixture was stirred vigorously for 5 min. The phases were separated and the aqueous phase was extracted with dichloromethane (100 mL). The combined organic phases were dried over magnesium sulfate, and the solvent was removed in vacuo. The crude product was purified by column chromatography to give 7-benzyl-3-methyl-5,6,7,8-tetrahydro-2,7-naphthyridine-4-carbonitrile as a colorless oil (8.9 g, 53% yield).

Workup

  1. stirringthe resulting mixture was stirred vigorously for 5 min
  2. customThe phases were separated
  3. extractionthe aqueous phase was extracted with dichloromethane (100 mL)
  4. dry with materialThe combined organic phases were dried over magnesium sulfate
  5. customthe solvent was removed in vacuo
  6. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-00b42c5ad9cb424a8ef868590290e997
Source dataset
uspto-grants-2007_11
Patent number
US07297700B2

Reaction notes

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