Hydrochloric Acid → Orm-10103

HRID 31166Notes

Reaction equation

HRID 31166 reaction equation
[F-].[K+].[C:3]1([CH:9]2[CH2:18][CH2:17][C:16]3[C:11](=[CH:12][CH:13]=[C:14]([OH:19])[CH:15]=3)[O:10]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl[C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][N:22]=1.Cl>CN(C=O)C>[N+:27]([C:24]1[CH:25]=[CH:26][C:21]([O:19][C:14]2[CH:15]=[C:16]3[C:11](=[CH:12][CH:13]=2)[O:10][CH:9]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:18][CH2:17]3)=[N:22][CH:23]=1)([O-:29])=[O:28]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 783082-Chloro-5-nitropyridineHCID 522689Potassium FluorideHCID 212875382-Phenylchroman-6-ol

Product 1

HCID 17978512Orm-10103

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

Potassium fluoride (225 mg) was added into a solution of 2-phenylchroman-6-ol (300 mg) in dry DMF (3 ml). After stirring the resulting mixture at 120° C. for 30 minutes 2-chloro-5-nitropyridine (195 mg) was added. The reaction mixture was stirred for a further 6½ hours at 120° C. After cooling into room temperature 1 M HCl-solution was added and the mixture was extracted with ethyl acetate. The combined organic layers were washed with water then with saturated NaCl-solution and dried with Na2SO4. 5-Nitro-2-(2-phenylchroman-6-yloxy)pyridine was recrystallised from acetone-2-propanol (1:5). 1H NMR (400 MHz, d6-DMSO) δ: 9.00 (d, 1H, J 2.9 Hz), 8.60 (dd, 1H, J 9.2, 2.9 Hz), 7.47-7.32 (m, 5H), 7.20 (d, 1H, J 9.2 Hz), 7.00-6.89 (m, 3H), 5.15 (dd, 1H, J 10.1, 2.2 Hz), 2.99 (ddd, 1H, J −16.8, 11.3, 6.2 Hz), 2.75 (ddd, 1H, J −16.8, 5.4, 3.3 Hz), 2.18 (m, 1H), 2.02 (m, 1H).

Workup

  1. additionwas added
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe combined organic layers were washed with water
  5. dry with materialwith saturated NaCl-solution and dried with Na2SO4
  6. custom5-Nitro-2-(2-phenylchroman-6-yloxy)pyridine was recrystallised from acetone-2-propanol (1:5)

Sources & evidence

ORD record
ord-69413d5a03ba4372b64d1d5977905712
Source dataset
uspto-grants-2008_09
Patent number
US07425568B2

Reaction notes

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