Nitric Acid → HCID 89726382, compound

HRID 1777766Notes

Reaction equation

HRID 1777766 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:13]=[CH:12][C:10]([NH2:11])=[CH:9][CH:8]=2)[N:3]=1.[C:14]([O:17]C(=O)C)(=O)[CH3:15].[N+:21]([O-])([OH:23])=[O:22]>>[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:13]=[CH:12][C:10]([NH:11][C:14](=[O:17])[CH3:15])=[C:9]([N+:21]([O-:23])=[O:22])[CH:8]=2)[N:3]=1

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 7918Acetic AnhydrideHCID 181881764-(5-Methyl-1,2,4-oxadiazol-3-yl)aniline

Product 1

HCID 89726382HCID 89726382, compound

Conditions

Temperature
10 °C

Procedure

4-(5-Methyl-1,2,4-oxadiazol-3-yl)aniline (500 mg) was added to acetic anhydride (2.1 mL) over 10 min and the mixture was cooled down to 10° C. HNO3 (65% in water, 0.59 mL) was added slowly to keep the temperature of the reaction mixture below 15° C. After the end of the addition, the reaction mixture was allowed to warm to RT over 1 h, was quenched with ice-cold water and stirred for 10 min. The resulting mixture was basified with aq. NH4OH (25%) to pH=12 and extracted with DCM. The phases were separated and the org. phase was evaporated in vacuo. LC-MS (B): tR=0.75 min; [M]+: 262.05.

Workup

  1. customthe temperature of the reaction mixture below 15° C
  2. additionAfter the end of the addition
  3. temperatureto warm to RT over 1 h
  4. customwas quenched with ice-cold water
  5. extractionextracted with DCM
  6. customThe phases were separated
  7. customphase was evaporated in vacuo

Sources & evidence

ORD record
ord-fff46ba18c2e434584e7709d68adae61
Source dataset
uspto-grants-2016_02
Patent number
US09266876B2

Reaction notes

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