Acetic Acid → HCID 23338818, compound

HRID 28085

Reaction equation

HRID 28085 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]=[C:9]([OH:12])[CH:8]=[CH:7]2.[N+:13]([C:16]1[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1)([O-:15])=[O:14].CC(O)=O>N1C=CC=CC=1.CCCCCC>[N+:13]([C:16]1[CH:17]=[CH:18][C:19]([S:22]([NH:1][C:2]2[CH:3]=[CH:4][CH:5]=[C:6]3[C:11]=2[CH:10]=[C:9]([OH:12])[CH:8]=[CH:7]3)(=[O:24])=[O:23])=[CH:20][CH:21]=1)([O-:15])=[O:14]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 74044-Nitrobenzenesulfonyl chlorideHCID 83588-Amino-2-naphthalenol

Product 1

HCID 23338818HCID 23338818, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8058HexaneSolvent

Procedure

A mixture of 8-amino-2-hydroxynapthalene (50 g, 0.3 mole) and 4-nitrobenzenesulfonyl chloride (55 g, 0.25 mole) in pyridine (500 ml) was heated under reflux for 2.5 hours then allowed to stand O/N. The mixture was poured in ice water and acidified with HOAc. The precipitated product was boiled in hexane and then recrystallized from ethyl acetate-hexane to give 40 g of green product (47%). This material was used in Part B.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2.5 hours
  3. customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-48bc3295670e4b13b17c66856ba7b49d
Source dataset
uspto-grants-1980_09
Patent number
US04225526

Linked notes

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