Hydrochloric Acid → N-(3-hydroxynaphthalen-2-yl)acetamide

HRID 1474514Notes

Reaction equation

HRID 1474514 reaction equation
[NH2:1][C:2]1[C:3]([OH:12])=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.C(=O)([O-])[O-].[Na+].[Na+].[C:19](Cl)(=[O:21])[CH3:20].Cl>CC(C)=O>[OH:12][C:3]1[C:2]([NH:1][C:19](=[O:21])[CH3:20])=[CH:11][C:10]2[C:5]([CH:4]=1)=[CH:6][CH:7]=[CH:8][CH:9]=2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 10340Sodium CarbonateHCID 794493-Amino-2-naphthol

Product 1

HCID 15881733N-(3-hydroxynaphthalen-2-yl)acetamideYield 78%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
0 °C

Procedure

An acetone solution (60 ml) of 3-amino-2-naphthol (5.0 g, 31.4 mmol) was added to an aqueous solution (20 ml) of sodium carbonate (4.77 g, 34.5 mmol). The mixture was cooled in an ice-water bath, and then acetyl chloride (2.27 ml, 32.0 mmol) was added to the mixture dropwise over 5 minutes. The resulting mixture was stirred at 0° C. for 4 hours and then allowed to stand at room temperature overnight. 2N Hydrochloric acid was added to the reaction mixture to adjust its pH to 3. The generated insoluble matter was separated, washed with water, and then dried, giving a white powder of N-(3-hydroxynaphthalen-2-yl)acetamide (4.9 g, yield: 78%).

Workup

  1. temperatureThe mixture was cooled in an ice-water bath
  2. waitto stand at room temperature overnight
  3. customThe generated insoluble matter was separated
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-89cb85ffac28411eb23f2121dcb5ce84
Source dataset
uspto-grants-2015_04
Patent number
US09018229B2

Reaction notes

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