Hydrochloric Acid → HCID 17978577, compound

HRID 31234Notes

Reaction equation

HRID 31234 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:6][CH2:5]2.[F-].[K+].Cl[C:21]1[C:26]([N+:27]([O-:29])=[O:28])=[CH:25][CH:24]=[CH:23][N:22]=1.Cl>CN(C=O)C.O.CCOC(C)=O>[N+:27]([C:26]1[C:21]([O:1][C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[O:8][CH:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:6][CH2:5]3)=[N:22][CH:23]=[CH:24][CH:25]=1)([O-:29])=[O:28]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 796132-Chloro-3-nitropyridineHCID 522689Potassium FluorideHCID 212875382-Phenylchroman-6-ol

Product 1

HCID 17978577HCID 17978577, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

6-Hydroxyflavane (0.150 g) was dissolved in 3 ml of dry DMF under nitrogen. KF (0.117 g) was added and the solution was stirred for 30 minutes at +120° C. The solution was cooled a bit and 2-chloro-3-nitropyridine was added (0.212 g) and stirred for 7 hours at +120° C. and overnight at room temperature. The reaction mixture was taken up with EtOAc and 1M HCl and water were added and phases separated. Organic phase was washed with water and pH was adjusted to 7 with 1M NaOH. Organic phase was washed with water, brine and dried over Na2SO4. Product was purified by column chromatography (CH2Cl2:n-heptane/80:20). 1H-NMR (400 MHz; d6-DMSO): δ 8.55 (dd, 1H, J=7.9 Hz, J=1.7 Hz), 8.42 (dd, 1H, J=4.9 Hz, J=1.7 Hz), 7.51-7.29 (m, 6H), 7.02-6.92 (m, 2H), 6.88 (d, 1H, J=8.7 Hz), 5.14 (dd, 1H, J=10.0 Hz, J=2.1 Hz), 3.05-2.92 (m, 1H), 2.78-2.68 (m, 1H), 2.22-2.13 (m, 1H), 2.07-1.95 (m, 1H).

Workup

  1. additionwas added (0.212 g)
  2. stirringstirred for 7 hours at +120° C. and overnight at room temperature
  3. additionwere added
  4. customphases separated
  5. washOrganic phase was washed with water and pH
  6. washOrganic phase was washed with water, brine
  7. dry with materialdried over Na2SO4
  8. customProduct was purified by column chromatography (CH2Cl2:n-heptane/80:20)

Sources & evidence

ORD record
ord-fa369d281e694c2cafc2edb9ed50cc9a
Source dataset
uspto-grants-2008_09
Patent number
US07425568B2

Reaction notes

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