2-Nitroaniline → HCID 2841246, compound

HRID 861913Notes

Reaction equation

HRID 861913 reaction equation
[C:1]12([C:11](Cl)=[O:12])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[N+:14]([C:17]1[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=1[NH2:19])([O-:16])=[O:15].C(N(CC)CC)C>CC(C)=O>[C:1]12([C:11]([NH:19][C:18]3[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=3[N+:14]([O-:16])=[O:15])=[O:12])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

Participants

5

Reactant 3

HCID 69462-NitroanilineHCID 8471TriethylamineHCID 989151-Adamantanecarbonyl chloride

Product 1

HCID 2841246HCID 2841246, compoundYield 76.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent3×

Procedure

A solution of 1-adamantanecarbonyl chloride (17.95 g) in acetone (60 ml) was dropped into a solution of 2-nitroaniline (10.4 g) and triethylamine (12.6 ml) in acetone (50 ml), at ° under a nitrogen atmosphere. The mixture was stirred at 23° for 22 h; then further acetone (50 ml) was added. The mixture was heated at 70° for 3 h. The mixture was allowed to cool to 23°, then filtered; the brown solid obtained was crystallized from acetone to give the title compound as a yellow solid (17.3 g). T.l.c. CH-EA (10:2), Rf 0.67. M.p. 111°-4°.

Workup

  1. temperatureThe mixture was heated at 70° for 3 h
  2. temperatureto cool to 23°
  3. filtrationfiltered
  4. customthe brown solid obtained
  5. customwas crystallized from acetone

Sources & evidence

ORD record
ord-774140ce767c4de5a1e36ef2d611a4a1
Source dataset
uspto-grants-1998_02
Patent number
US05716953

Reaction notes

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