2-Naphthoic acid → 2-Naphthalen-2-yl-benzooxazol-5-yl-amine

HRID 63026

Reaction equation

HRID 63026 reaction equation
[CH:1]1[C:6]([NH2:7])=[CH:5][C:4]([NH2:8])=[C:3]([OH:9])[CH:2]=1.Cl.Cl.[CH:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][C:13]=1[C:22](O)=O.[OH-].[Na+]>>[CH:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][C:13]=1[C:22]1[O:9][C:3]2[CH:2]=[CH:1][C:6]([NH2:7])=[CH:5][C:4]=2[N:8]=1

Participants

4

Reactant 3

HCID 71232-Naphthoic acidHCID 87152,4-Diaminophenol hydrochlorideHCID 14798Sodium Hydroxide

Product 1

HCID 7360122-Naphthalen-2-yl-benzooxazol-5-yl-amineYield 75%

Conditions

Temperature
180 °C

Procedure

80 μmol of 2,4-diaminophenol.2HCl and 80 μmol of naphthalene-2-carboxylic acid were dissolved in 100 mg of PPA, and then, the mixed solution was stirred at a temperature of 180° C. for 3 to 4 hours. After completion of the reaction, the reaction solution was cooled, neutralized with 10% NaOH, and filtered by using distilled water for recrystallization in a slow manner, thereby obtaining 15.6 mg of 2-(naphthalene-2-yl)benzo[d]oxazole-5-amine (Derivative #3) (yield: 75%).

Workup

  1. customAfter completion of the reaction
  2. temperaturethe reaction solution was cooled
  3. filtrationfiltered
  4. distillationby using distilled water
  5. customfor recrystallization in a slow manner

Sources & evidence

ORD record
ord-bf87e7cb139f4e8ea7b4af588f1a563f
Source dataset
uspto-grants-2016_09
Patent number
US09447054B2

Linked notes

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