Pyridine → HCID 19387978, compound

HRID 1757467Notes

Reaction equation

HRID 1757467 reaction equation
[N+:1]([C:4]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:5]=1[NH2:6])([O-:3])=[O:2].N1C=CC=CC=1.[C:19]12([C:29]3[CH:30]=[C:31]([CH:35]=[CH:36][C:37]=3[O:38][CH3:39])[C:32](Cl)=[O:33])[CH2:28][CH:23]3[CH2:24][CH:25]([CH2:27][CH:21]([CH2:22]3)[CH2:20]1)[CH2:26]2.CCCCCC>ClCCl>[CH3:12][O:11][C:9]1[CH:8]=[CH:7][C:5]([NH:6][C:32](=[O:33])[C:31]2[CH:35]=[CH:36][C:37]([O:38][CH3:39])=[C:29]([C:19]34[CH2:28][CH:23]5[CH2:22][CH:21]([CH2:27][CH:25]([CH2:24]5)[CH2:26]3)[CH2:20]4)[CH:30]=2)=[C:4]([N+:1]([O-:3])=[O:2])[CH:10]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 8058HexaneHCID 667934-Methoxy-2-nitroanilineHCID 108044973-(1-Adamantyl)-4-methoxybenzoyl chloride

Product 1

HCID 19387978HCID 19387978, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5.38 g (32 mM) of 2-nitro-4-methoxyaniline and 50 ml of pyridine are introduced into a round-bottomed flask. 9.7 g (32 mM) of 3-(1-adamantyl)-4-methoxybenzoic acid chloride, dissolved in 100 ml of dichloromethane, are then added dropwise. At the end of addition, the mixture is brought to reflux for 12 hours. After having cooled, 100 ml of hexane are added and the precipitate obtained is recovered by filtration and washed with a mixture containing 10% ether and 90% hexane and then with water. After drying, there are obtained 12.5 g (89%) of the expected product. M.p.=208°-210° C.

Workup

  1. additionare then added dropwise
  2. additionAt the end of addition
  3. temperatureto reflux for 12 hours
  4. temperatureAfter having cooled
  5. customthe precipitate obtained
  6. filtrationis recovered by filtration
  7. washwashed with a mixture
  8. additioncontaining 10% ether and 90% hexane
  9. customAfter drying

Sources & evidence

ORD record
ord-f9427406183344daad751446e5c02efc
Source dataset
uspto-grants-1995_08
Patent number
US05446059

Reaction notes

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