Acetic Anhydride → HCID 14722249, compound

HRID 1639019Notes

Reaction equation

HRID 1639019 reaction equation
[CH:1]1([NH:7][C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([O:18][C:19](=[O:21])[CH3:20])=[C:10]([O:22][CH3:23])[CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:24](OC(=O)C)(=[O:26])[CH3:25]>[Cl-].[Zn+2].[Cl-]>[C:24]([N:7]([CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1)[C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([O:18][C:19](=[O:21])[CH3:20])=[C:10]([O:22][CH3:23])[CH:9]=1)(=[O:26])[CH3:25]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 14722248HCID 14722248, compound

Product 1

HCID 14722249HCID 14722249, compound

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

A solution 5.0 g of 4-(cyclohexylamino)-1-acetoxy-2-methoxynaphthalene in 75 ml of acetic anhydride is stirred with 500 mg of zinc chloride in at 160°-170° C. for 2 hours. The reaction is cooled, filtered and evaporated under reduced pressure. The residue is taken up in 300 ml of diethyl ether and washed with 100 ml of water and then with 100 ml of brine. The organic solvent is dried over magnesium sulfate, filtered, and evaporated to dryness. The residue is crystallized from 120 ml of 2:1 diethyl ether-hexane to yield 4-(N-acetylcyclohexylamino)-1-acetoxy-2-methoxynaphthalene, m.p. 137°-139° C.

Workup

  1. temperatureThe reaction is cooled
  2. filtrationfiltered
  3. customevaporated under reduced pressure
  4. washwashed with 100 ml of water
  5. dry with materialThe organic solvent is dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customThe residue is crystallized from 120 ml of 2:1 diethyl ether-hexane

Sources & evidence

ORD record
ord-563818c3657a4d0ca235bb9d8641c5ad
Source dataset
uspto-grants-1989_11
Patent number
US04882339

Reaction notes

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