Pyridine → HCID 13660395, compound

HRID 903976Notes

Reaction equation

HRID 903976 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[CH3:5][O:6][C:7]1[C:8](=[O:21])[C:9]2[C:14]([C:15](=[O:19])[C:16]=1[O:17][CH3:18])=[C:13]([NH2:20])[CH:12]=[CH:11][CH:10]=2.N1C=CC=CC=1>C(Cl)(Cl)Cl>[CH3:5][O:6][C:7]1[C:8](=[O:21])[C:9]2[C:14]([C:15](=[O:19])[C:16]=1[O:17][CH3:18])=[C:13]([NH:20][C:1](=[O:3])[CH3:2])[CH:12]=[CH:11][CH:10]=2

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 122506961,4-Naphthalenedione, 5-amino-2,3-dimethoxy-

Product 1

HCID 13660395HCID 13660395, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

Acetyl chloride (1.5 ml, 20 mmol) is added dropwise, over 10 min, to an ice water cooled, stirred suspension of 12a from Example 5 (466 mg, 2 mmol) in chloroform (15 ml) containing pyridine (1.6 ml, 20 mmol). After a total reaction time of 30 min, the mixture is diluted with chloroform (50 ml) and then washed with water (2×25 ml). The chloroform phase is dried over MgSO4, concentrated to dryness and the residue recrystallized from iso-propanol affording 498 mg (85%) of 12b R1 =R2 =OCH3, with mp 162°-163°.

Workup

  1. temperaturecooled
  2. washwashed with water (2×25 ml)
  3. dry with materialThe chloroform phase is dried over MgSO4
  4. concentrationconcentrated to dryness
  5. customthe residue recrystallized from iso-propanol affording 498 mg (85%) of 12b R1 =R2 =OCH3, with mp 162°-163°

Sources & evidence

ORD record
ord-debdf026d46346809f85dc982f4a9d7c
Source dataset
uspto-grants-1980_10
Patent number
US04229478

Reaction notes

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