Chloroethane → 2-Naphthalenesulfonic acid, 5-amino-6-ethoxy-

HRID 1759513Notes

Reaction equation

HRID 1759513 reaction equation
[NH:1]([C:5]1[C:14]2[C:9](=[CH:10][C:11]([S:15]([OH:18])(=[O:17])=[O:16])=[CH:12][CH:13]=2)[CH:8]=[CH:7][C:6]=1[OH:19])C(C)=O.C(=O)([O-])[O-].[K+].[K+].[OH-].[K+].[CH2:28](Cl)[CH3:29]>C(O)C>[NH2:1][C:5]1[C:14]2[C:9](=[CH:10][C:11]([S:15]([OH:18])(=[O:16])=[O:17])=[CH:12][CH:13]=2)[CH:8]=[CH:7][C:6]=1[O:19][CH2:28][CH3:29]

Participants

6

Reactant 4

HCID 6337ChloroethaneHCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 133359N-Acetyl-(1-amino-2-naphthol-6-sulfonic acid)

Product 1

HCID 2221662-Naphthalenesulfonic acid, 5-amino-6-ethoxy-Yield 113.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
120 °C

Procedure

98.1 g of 1-acetamino-2-hydroxy-naphthalene-6-sulphonic acid (71.7% pure=50.4 g of 100% pure=0.25 mol), prepared according to Example 4, are introduced into a 1.3 l autoclave. 34.6 g (0.25 mol) of potassium carbonate suspended in 500 ml of ethanol are added thereto. After heating the mixture to 120° C., 115 ml of 2 N potassium hydroxide solution and 54 ml (74 g=0.75 mol) of ethyl chloride are simultaneously pumped in. The reaction mixture is allowed to cool somewhat, the salt residue is filtered off and, after adding 100 g of water, 460 g of ethanol (water-containing) are distilled off from the filtrate. 50 ml of 50% strength sodium hydroxide solution are added dropwise to the mixture at a temperature of 98° C. After 2 hours, the reaction mixture is cooled to room temperature and the product which has precipitated is filtered off and washed with 100 ml of saturated sodium chloride solution. After filtering off and drying, 76.1 g of 1-amino-2-ethoxy-naphthalene-6-sulphonic acid (78.3% pure=60.0 g of 100% pure=90% of theory, relative to 1-acetamino-2-hydroxy-naphthalene-6-sulphonic acid, or 69.4% of theory, relative to 2-hydroxy-naphthalene-6-sulphonic acid) are obtained.

Workup

  1. additionare introduced into a 1.3 l autoclave
  2. additionare added
  3. temperatureto cool somewhat
  4. filtrationthe salt residue is filtered off
  5. additionafter adding 100 g of water, 460 g of ethanol (water-containing)
  6. distillationare distilled off from the filtrate
  7. addition50 ml of 50% strength sodium hydroxide solution are added dropwise to the mixture at a temperature of 98° C
  8. temperaturethe reaction mixture is cooled to room temperature
  9. customthe product which has precipitated
  10. filtrationis filtered off
  11. washwashed with 100 ml of saturated sodium chloride solution
  12. filtrationAfter filtering off
  13. customdrying

Sources & evidence

ORD record
ord-3c0c6a257c384167b4df607bf357ae87
Source dataset
uspto-grants-1982_07
Patent number
US04341719

Reaction notes

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