1-Chlorododecane → HCID 21473719, compound

HRID 2293996Notes

Reaction equation

HRID 2293996 reaction equation
[NH2:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[OH-].[Na+].Cl[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]>[Cl-].C[N+](CCCCCCCC)(CCCCCCCC)CCCCCCCC.C1C=CC=CC=1>[CH2:23]([O:8][C:7]1[C:2]([NH2:1])=[N:3][CH:4]=[CH:5][CH:6]=1)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH3:12]

Participants

6

Reactant 3

HCID 81921-ChlorododecaneHCID 14798Sodium HydroxideHCID 281142-Amino-3-Hydroxypyridine

Product 1

HCID 21473719HCID 21473719, compoundYield 75.4%

Reagents, catalysts & solvents 2

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 241BenzeneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-amino-3-pyridinol (0.10 mol), sodium hydroxide (50%) (30 ml), 1-chlorododecane (0.20 mol) and methyl-tri-octylammonium chloride (8 g) in benzene (300 ml) was stirred overnight at 80° C. The reaction mixture was cooled. The organic layer was separated, washed with 2N NaOH, dried (MgSO4), filtered and the solvent was evaporated. The residue was cooled and the resulting precipitate was filtered off, washed with hexane, petroleum ether and dried, yielding 21 g (75%) of 3-(dodecyloxy)-2-pyridinamine (interm. 2).

Workup

  1. temperatureThe reaction mixture was cooled
  2. customThe organic layer was separated
  3. washwashed with 2N NaOH
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent was evaporated
  7. temperatureThe residue was cooled
  8. filtrationthe resulting precipitate was filtered off
  9. washwashed with hexane, petroleum ether
  10. customdried

Sources & evidence

ORD record
ord-9aa6699a644a4ee897a3d68bd56e24d5
Source dataset
uspto-grants-1997_11
Patent number
US05688799

Reaction notes

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