Water → HCID 22566510, compound

HRID 25778Notes

Reaction equation

HRID 25778 reaction equation
[N:1]([CH2:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[O:21][CH3:22])[CH:13]=2)[NH:8][C:7]([CH3:24])([CH3:23])[CH:6]=1)=[N+]=[N-].C1COCC1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>CCOCC>[NH2:1][CH2:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[O:21][CH3:22])[CH:13]=2)[NH:8][C:7]([CH3:24])([CH3:23])[CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 22566521HCID 22566521, compound

Product 1

HCID 22566510HCID 22566510, compoundYield 73.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A round bottom flask equipped with a stir bar was charged with 4-azidomethyl-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline (0.565 mmol) and THF (4.2 mL). The system was placed under argon, after which PPh3 (0.621 mmol, 1.1 equiv) and water (0.621 mmol, 1.1 equiv) were added. The reaction was stirred overnight at room temperature. The crude reaction mixture was diluted with ether and filtered through diatomaceous earth until no more precipitate formed. The diatomaceous earth was washed well with ether. The organic layer was acidified with concentrated HCl affording a white fluffy precipitate which then oiled out. This layer was diluted with water and separated from the aqueous layer. The aqueous layer was then neutralized with Na2CO3 and extracted with methylene chloride. The organic extracts were combined and concentrated in vacuo to afford 122 mg of 4-aminomethyl-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline.

Workup

  1. customA round bottom flask equipped with a stir bar
  2. customThe crude reaction mixture
  3. filtrationfiltered through diatomaceous earth until no more precipitate
  4. customformed
  5. washThe diatomaceous earth was washed well with ether
  6. additionThis layer was diluted with water
  7. customseparated from the aqueous layer
  8. extractionextracted with methylene chloride
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-60201001f87b4e79bcefd4fa9fd836c2
Source dataset
uspto-grants-2005_02
Patent number
US06858627B2

Reaction notes

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