Sodium Hydroxide → 4-(4-tert-Butylanilino)-3-methoxy-2-methylpyridine

HRID 1010

Reaction equation

HRID 1010 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH3:8])[C:3]=1[O:9][CH3:10].[C:11]([C:15]1[CH:21]=[CH:20][C:18]([NH2:19])=[CH:17][CH:16]=1)([CH3:14])([CH3:13])[CH3:12].[OH-].[Na+]>C1(O)C=CC=CC=1>[C:11]([C:15]1[CH:16]=[CH:17][C:18]([NH:19][C:2]2[CH:7]=[CH:6][N:5]=[C:4]([CH3:8])[C:3]=2[O:9][CH3:10])=[CH:20][CH:21]=1)([CH3:14])([CH3:12])[CH3:13]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 698614-Tert-ButylanilineHCID 105830464-Chloro-3-methoxy-2-methylpyridine

Product 1

HCID 196939534-(4-tert-Butylanilino)-3-methoxy-2-methylpyridine

Reagents, catalysts & solvents 1

HCID 996PhenolSolvent

Procedure

7.9 g of 4-chloro-3-methoxy-2-methylpyridine and 22.4 g of 4-tert-butylaniline are heated at 120° C. for 8 hours in 20 g of phenol. After cooling, the mixture is poured into NaOH and the product is extracted using methylene chloride. After concentrating, the excess of amine is distilled off in vacuo and the residue is crystallized using hexane. 9.5 g=55%

Workup

  1. temperatureAfter cooling
  2. extractionthe product is extracted
  3. concentrationAfter concentrating
  4. distillationthe excess of amine is distilled off in vacuo
  5. customthe residue is crystallized

Sources & evidence

ORD record
ord-ed5d30e63cae482aa9ed8a44a63361f9
Source dataset
uspto-grants-1998_03
Patent number
US05723450

Linked notes

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