Ammonia → HCID 178432074, compound

HRID 452174Notes

Reaction equation

HRID 452174 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:5]=[C:6]([CH3:9])[C:7]=1[NH2:8].[C:16](OC)(OC)(OC)[CH3:17].N>C(O)(=O)C>[CH3:16][C:17]1[NH:8][C:7]2[C:6]([CH3:9])=[CH:5][C:4]([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)=[CH:3][C:2]=2[N:1]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 15050Trimethyl orthoacetateHCID 672110583,4-Diamino-5-methylbiphenyl

Product 1

HCID 178432074HCID 178432074, compoundYield 96.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
110 °C

Procedure

[step 4] 3,4-Diamino-5-methylbiphenyl (150 mg, 0.64 mmol) obtained in step 3 was suspended in acetic acid (4 mL), trimethyl ortho acetate (0.14 mL, 0.76 mmol) was added, and the mixture was stirred at 110° C. for 18 hr. Under ice-cooling, 28% aqueous ammonia solution (5 mL) was added to the mixture, and the mixture was extracted with ethyl acetate (20 mL). The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give the title compound (137 mg, 96%).

Workup

  1. temperatureUnder ice-cooling
  2. extractionthe mixture was extracted with ethyl acetate (20 mL)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7a2d765bc5874b85a76baa42c5dc00b5
Source dataset
uspto-grants-2013_07
Patent number
US08486980B2

Reaction notes

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