Hydrochloric Acid → HCID 17978530, compound

HRID 31223Notes

Reaction equation

HRID 31223 reaction equation
[C:1]1([CH:7]2[CH2:16][CH2:15][C:14]3[CH:13]=[C:12]([OH:17])[CH:11]=[CH:10][C:9]=3[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][N:20]=1.[F-].[K+].Cl>CN(C)C=O.O>[N+:25]([C:22]1[CH:23]=[CH:24][C:19]([O:17][C:12]2[CH:11]=[CH:10][C:9]3[CH2:8][CH:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[CH2:16][CH2:15][C:14]=3[CH:13]=2)=[N:20][CH:21]=1)([O-:27])=[O:26]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 783082-Chloro-5-nitropyridineHCID 522689Potassium FluorideHCID 18689857HCID 18689857, compound

Product 1

HCID 17978530HCID 17978530, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

6-Phenyl-5,6,7,8-tetrahydro-naphthalen-2-ol (30 mg), 2-chloro-5-nitropyridine (21 mg) and potassium fluoride (23 mg) in dry dimethylformamide were heated at 120° C. until disappearance of the starting material. Water and 1 N HCl were added and the mixture extracted with ethyl acetate. Ethyl acetate was washed with brine and water, dried and evaporated. The product was recrystallised from toluene. 1H NMR (400 MHz, d6-DMSO) δ: 9.04 (d, 1H, J 2.4 Hz), 8.61 (dd, 1H, J 9.0, 2.5), 7.18-7.35 (m, 7H), 6.95-6.99 (m, 2H), 2.83-3.01 (m, 5H), 1.87-2.04 (m, 2H).

Workup

  1. extractionthe mixture extracted with ethyl acetate
  2. washEthyl acetate was washed with brine and water
  3. customdried
  4. customevaporated
  5. customThe product was recrystallised from toluene

Sources & evidence

ORD record
ord-4a0d965088e449c2a298dee8686c7b97
Source dataset
uspto-grants-2008_09
Patent number
US07425568B2

Reaction notes

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