Acetic Anhydride → HCID 19925747, compound

HRID 1697860Notes

Reaction equation

HRID 1697860 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([C:12]([OH:14])=[O:13])=[CH:7][CH:6]=[CH:5]2.[C:15](OC(=O)C)(=[O:17])[CH3:16]>S(=O)(=O)(O)O.O>[C:15]([O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([C:12]([OH:14])=[O:13])=[CH:7][CH:6]=[CH:5]2)(=[O:17])[CH3:16]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 54638006-Hydroxy-1-naphthoic acid

Product 1

HCID 19925747HCID 19925747, compound

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 962WaterSolvent

Procedure

6-Hydroxy-1-naphthoic acid (1 g) was mixed with acetic anhydride (5 ml) and sulfuric acid (5 drops). The mixture was refluxed for 3 hours and cooled at RT for 10 hours then mixed with water (15 ml). The solid was filtered and washed with water and cold MeOH to give the product as 6-acetoxy-1-naphthoic acid (900 mg) that was mixed with EDC (1.5 eq), HOBt (1 eq), MeNH2—HCl (2.5 eq, methylamine hydrochloride) and DIPEA (2.5 eq) in DCM (25 ml). The reaction was stirred at RT overnight and washed with NaHCO3 solution, dried. The solution was evaporated and mixed with 15% KOH (2 ml) in MeOH (10 ml) further stirred at RT for 30 minutes. The solvent was evaporated and the residue was adjusted to weak acidic with 2N HCl, the solid was filtered and washed with water twice and cold MeOH to give 6-Hydroxy-N-methyl-1-naphthamide (720 mg).

Workup

  1. temperatureThe mixture was refluxed for 3 hours
  2. filtrationThe solid was filtered
  3. washwashed with water and cold MeOH

Sources & evidence

ORD record
ord-afe8789ff6034c67b82e4c1c31c38c5a
Source dataset
uspto-grants-2012_04
Patent number
US08163923B2

Reaction notes

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