1H,3H-Naphtho[1,8-cd]pyran-1,3-dione, 6-chloro- → HCID 14281447, compound

HRID 2231224Notes

Reaction equation

HRID 2231224 reaction equation
[CH:1]1[CH:10]=[C:9]2[C:11]([O:13][C:14](=[O:15])[C:7]3=[C:8]2[C:3](=[C:4]([Cl:16])[CH:5]=[CH:6]3)[CH:2]=1)=O.[N:17]1([CH2:22][CH2:23][CH2:24][CH2:25][NH2:26])[CH:21]=[CH:20][N:19]=[CH:18]1>C(O)C>[ClH:16].[Cl:16][C:4]1[CH:5]=[CH:6][C:7]2[C:14](=[O:15])[N:26]([CH2:25][CH2:24][CH2:23][CH2:22][N:17]3[CH:21]=[CH:20][N:19]=[CH:18]3)[C:11](=[O:13])[C:9]3[C:8]=2[C:3]=1[CH:2]=[CH:1][CH:10]=3

Participants

4

Reactant 2

HCID 776721H,3H-Naphtho[1,8-cd]pyran-1,3-dione, 6-chloro-HCID 43794804-(1H-imidazol-1-yl)butan-1-amine

Product 1

HCID 14281447HCID 14281447, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3.49 g of 4-chloro-1,8-naphthalic anhydride, 50 ml of ethanol and 2.1 g of 1H-imidazol-1butanamine as stirred at room temperature for 5 hours and concentrated. The residue was washed on to a funnel with a little ethanol, washed with ether and dried in vacuo. The solid material, 3.72 g, was mixed with 15 ml of acetic anhydride and 5 ml of acetic acid and heated at 110°-120° C. in an oil bath for 6 hours. The reaction mixture was concentrated and shaken with 20 ml of 1N sodium hydroxide and 150 ml of methylene chloride and the layers were separated. The organic layer was washed with water, dried over magnesium sulfate and concentrated. The residue was recrystallized from ethyl acetate to obtain the desired product, mp 138°-140° C.

Workup

  1. concentrationconcentrated
  2. washThe residue was washed on to a funnel with a little ethanol
  3. washwashed with ether
  4. customdried in vacuo
  5. additionThe solid material, 3.72 g, was mixed with 15 ml of acetic anhydride and 5 ml of acetic acid
  6. temperatureheated at 110°-120° C. in an oil bath for 6 hours
  7. concentrationThe reaction mixture was concentrated
  8. stirringshaken with 20 ml of 1N sodium hydroxide and 150 ml of methylene chloride
  9. customthe layers were separated
  10. washThe organic layer was washed with water
  11. dry with materialdried over magnesium sulfate
  12. concentrationconcentrated
  13. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-8e3cadf4ba6e48ddbb64ef0e1ab13539
Source dataset
uspto-grants-1988_11
Patent number
US04782064

Reaction notes

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