Acetic Acid → HCID 20291868, compound

HRID 1413353Notes

Reaction equation

HRID 1413353 reaction equation
[N+:1]([C:4]1[CH:14]=[CH:13][CH:12]=[C:6]2[C:7]([O:9][C:10](=[O:11])[C:5]=12)=O)([O-:3])=[O:2].[NH2:15][C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[C:23]([OH:26])[CH:24]=2)[CH:19]=[CH:18][CH:17]=1.C(O)(=O)C>O>[N+:1]([C:4]1[CH:14]=[CH:13][CH:12]=[C:6]2[C:7]([N:15]([C:16]3[C:25]4[C:20](=[CH:21][CH:22]=[C:23]([OH:26])[CH:24]=4)[CH:19]=[CH:18][CH:17]=3)[C:10](=[O:11])[C:5]=12)=[O:9])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 83588-Amino-2-naphthalenolHCID 216313-Nitrophthalic anhydride

Product 1

HCID 20291868HCID 20291868, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The starting material used in the above example can be prepared as follows: A mixture of 1.93 g (0.01 mol) of 3-nitrophthalic anhydride, 1.59 g (0.01 mol) of 1-amino-7-naphthol and 30 ml of acetic acid is refluxed for 17 hours. The resulting suspension is stirred with 300 ml of water, then filtered and the filter residue is then washed with water and dried. 2.9 g of crude product are obtained and are extracted with chloroform. The chloroform extract is stirred with 4 g of silica gel, filtered with suction whilst hot, and evaporated to dryness. 2.4 g (72% of theory) of 1-(3-nitrophthalimidyl)-7-hydroxynaphthalene are obtained; melting point 136°-7° C.

Workup

  1. customcan be prepared
  2. temperatureis refluxed for 17 hours
  3. filtrationfiltered
  4. washthe filter residue is then washed with water
  5. customdried
  6. custom2.9 g of crude product are obtained
  7. extractionare extracted with chloroform
  8. extractionThe chloroform extract
  9. filtrationfiltered with suction whilst hot, and
  10. customevaporated to dryness

Sources & evidence

ORD record
ord-f3a0822644df4b5a83f145af4f05af4a
Source dataset
uspto-grants-1981_02
Patent number
US04250096

Reaction notes

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