6-Chloro-3-pyridinecarbonitrile → HCID 69017232, compound

HRID 1455081Notes

Reaction equation

HRID 1455081 reaction equation
[N+]([C:4]1[CH:5]=[CH:6][C:7]([O:10][C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[O:17][CH:16]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:15][CH2:14]3)=[N:8][CH:9]=1)([O-])=O.C1(C2CCC3C(=CC=C(O)C=3)O2)C=CC=CC=1.Cl[C:45]1C=CC(C#N)=C[N:46]=1>>[C:21]1([CH:16]2[CH2:15][CH2:14][C:13]3[C:18](=[CH:19][CH:20]=[C:11]([O:10][C:7]4[CH:6]=[CH:5][C:4]([C:45]#[N:46])=[CH:9][N:8]=4)[CH:12]=3)[O:17]2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 3

HCID 51520946-Chloro-3-pyridinecarbonitrileHCID 17978512Orm-10103HCID 212875382-Phenylchroman-6-ol

Product 1

HCID 69017232HCID 69017232, compound

Procedure

6-(2-Phenylchroman-6-yloxy)nicotinonitrile was prepared as described for 5-nitro-2-(2-phenylchroman-6-yloxy)pyridine in example 1 (b) using 500 mg of 2-phenylchroman-6-ol and replacing 2-chloro-5-nitropyridine by 337 mg of 6-chloro-nicotinonitrile. The product was purified by column chromatography using heptane-ethyl acetate as an eluant and then crystallised from 2-propanol. 1H NMR (400 MHz, d6-DMSO) δ: 8.65 (d, 1H, J 2.4 Hz), 8.28 (dd, 1H, 8.8, 2.4 Hz), 7.47-7.34 (m, 5H), 7.17 (d, 1H, J 8.8 Hz) 6.96-6.87 (m, 3H), 5.14 (dd, 1H, J 10.1, 2.2 Hz), 2.99 (m, 1H), 2.73 (m, 1H), 2.18 (m, 1H), 2.00 (m, 1H).

Workup

  1. customThe product was purified by column chromatography
  2. customcrystallised from 2-propanol

Sources & evidence

ORD record
ord-79641789383e44d1b11fd68e3eafbcdc
Source dataset
uspto-grants-2009_01
Patent number
US07482340B2

Reaction notes

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