Hydrochloric Acid → HCID 17978530, compound

HRID 1455026Notes

Reaction equation

HRID 1455026 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-2ba3768215e24b56bc8a48d68adc12de
Source dataset
uspto-grants-2009_01
Patent number
US07482340B2

Reaction notes

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