Pyridine → 2-(1-Chloro-indan-5-yl)-benzonitrile

HRID 1742405Notes

Reaction equation

HRID 1742405 reaction equation
O[CH:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]3[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=3[C:13]#[N:14])=[CH:8][CH:9]=2)[CH2:4][CH2:3]1.N1C=CC=CC=1.S(Cl)([Cl:27])=O>C(Cl)Cl>[Cl:27][CH:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]3[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=3[C:13]#[N:14])=[CH:8][CH:9]=2)[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 190089042-(1-Hydroxy-indan-5-yl)-benzonitrile

Product 1

HCID 152289522-(1-Chloro-indan-5-yl)-benzonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(1-hydroxy-indan-5-yl)-benzonitrile (3.3 grams, 14 mmol) and pyridine (2.4 mL, 30 mmol)in CH2Cl2 (30 mL) at 0° C. was added thionyl chloride (3.3 grams, 2.04 mL, 28 mmol). The reaction mixture was allowed to warm slowly to room temperature. After 1 hour, the reaction mixture was cooled to 0° C., quenched with saturated aqueous NaHCO3 (10 mL) and diluted with methylene chloride (CH2Cl2) (100 mL). The organic layer was separated and washed with saturated aqueous NaHCO3 (1×25 mL) and saturated aqueous NaCl (1×25 mL), dried (MgSO4) and concentrated in vacuo to give a yellow oil. 1H NMR (250 MHz, CDCl3): d 7.78 (1H, d), 7.65 (1H, t), 7.48 (m, 5 H), 5.48 (dd, 1 H), 3.25 (m, 1 H), 2.98 (m, 1 H), 2.67 (m, 1 H), 2.45 (m, 1 H).

Workup

  1. temperaturethe reaction mixture was cooled to 0° C.
  2. customquenched with saturated aqueous NaHCO3 (10 mL)
  3. additiondiluted with methylene chloride (CH2Cl2) (100 mL)
  4. customThe organic layer was separated
  5. washwashed with saturated aqueous NaHCO3 (1×25 mL) and saturated aqueous NaCl (1×25 mL)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customto give a yellow oil

Sources & evidence

ORD record
ord-77e4b30e27194991a341ac1571afb8ee
Source dataset
uspto-grants-1994_08
Patent number
US05338740

Reaction notes

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