P-Anisidine → HCID 136409737, compound

HRID 972426Notes

Reaction equation

HRID 972426 reaction equation
[OH:1][C:2]1[C:3]([CH2:15][CH2:16][CH2:17][CH2:18][O:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]([CH2:29][CH3:30])([CH3:28])[CH3:27])=[CH:22][C:21]=2[C:31]([CH2:34][CH3:35])([CH3:33])[CH3:32])=[C:4]([C:12]([NH2:14])=[O:13])[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[OH-].[Na+].[CH3:38][O:39][C:40]1[CH:45]=[CH:44][C:43]([NH2:46])=[CH:42][CH:41]=1.[N:47]([O-])=O.[Na+]>O1CCCC1.CO.O>[OH:1][C:2]1[C:3]([CH2:15][CH2:16][CH2:17][CH2:18][O:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]([CH2:29][CH3:30])([CH3:27])[CH3:28])=[CH:22][C:21]=2[C:31]([CH2:34][CH3:35])([CH3:33])[CH3:32])=[C:4]([C:12]([NH2:14])=[O:13])[C:5]2[C:10]([C:11]=1[N:47]=[N:46][C:43]1[CH:44]=[CH:45][C:40]([O:39][CH3:38])=[CH:41][CH:42]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

8

Reactant 4

HCID 7732P-AnisidineHCID 14798Sodium HydroxideHCID 21404062HCID 21404062, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 136409737HCID 136409737, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent3×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To 20 g (0.042 mole) of 3-hydroxy-2-[4-(2,4-di-t-pentylphenoxy)-n-butyl]naphthamide in 200 ml tetrahydrofuran was added a solution of 8 g sodium hydroxide in 200 ml methanol. The mixture was cooled to 0° C. and treated with a diazonium solution prepared from a solution of 5.2 g (0.042 mole) p-anisidine in 40 ml water containing 10 ml conc. hydrochloric acid and a solution of 2.9 g (0.042 mole) sodium nitrite in 30 ml water. Then 400 ml water was added, and the mixture was stirred at 0° C. for 2 hrs. and at room temperature for one hour. The oil which separated after acidification with 30 ml acetic acid was extracted with ether. The solution was dried and concentrated to 21 g of a red oil which was used without further purification in the next step.

Workup

  1. waitand at room temperature for one hour
  2. customThe oil which separated after acidification with 30 ml acetic acid
  3. extractionwas extracted with ether
  4. customThe solution was dried
  5. concentrationconcentrated to 21 g of a red oil which
  6. customwas used without further purification in the next step

Sources & evidence

ORD record
ord-6c1f01b400f745898e3297c58e1dddba
Source dataset
uspto-grants-1977_10
Patent number
US04053312

Reaction notes

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