Lithium Hydroxide → HCID 24860246, compound

HRID 538509Notes

Reaction equation

HRID 538509 reaction equation
[CH2:1]([O:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][N:18]=1)[C:14]#[N:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].C[O-:20].[Na+].[OH-].[Li+]>CO.O>[CH2:1]([O:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][N:18]=1)[C:14]([NH2:15])=[O:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

6

Reactant 3

HCID 3939Lithium HydroxideHCID 10942334Sodium MethoxideHCID 59402819HCID 59402819, compound

Product 1

HCID 24860246HCID 24860246, compoundYield 227%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

A solution of 2-(nonyloxy)isonicotinonitrile (250 mg, 1.0 mmol, 1 equiv.) and sodium methoxide (10 mg, 0.1 mmol, 0.1 equiv.) in dry CH3OH (10 ml) was stirred at r.t. for 2.5 h. A solution of lithium hydroxide (24 mg, 1.0 mmol, 1 equiv.) in water (1 ml) was added and the reaction mixture was heated under reflux for 3.5 h. After cooling at r.t., the mixture was poured into water (40 ml). The precipitant solid was filtered and dried in vacuo at 50° C., to give the desired compound as a white solid (60 mg, 23%), mp 108-110° C. HPLC-MS (method 1): m/z 265 [M+H]+, Rt=5.08 min.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 3.5 h
  3. filtrationThe precipitant solid was filtered
  4. customdried in vacuo at 50° C.

Sources & evidence

ORD record
ord-f7676cf820534ca0b82be09d48f28a25
Source dataset
uspto-grants-2014_10
Patent number
US08865736B2

Reaction notes

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