Sodium Azide → 2-(2-chloro-4-(2H-tetrazol-5-yl)phenyl)quinolin-6-ol

HRID 1507352Notes

Reaction equation

HRID 1507352 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[C:15]([OH:20])[CH:16]=2)[N:11]=1)[C:5]#[N:6].[N-:21]=[N+:22]=[N-:23].[Na+].[Li+].[Cl-]>COCCOCCO>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]2[N:21]=[N:22][NH:23][N:6]=2)[CH:7]=[CH:8][C:9]=1[C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[C:15]([OH:20])[CH:16]=2)[N:11]=1

Participants

5

Reactant 3

HCID 33557Sodium AzideHCID 433294Lithium ChlorideHCID 669801193-Chloro-4-(6-hydroxyquinolin-2-yl)benzonitrile

Product 1

HCID 1360789842-(2-chloro-4-(2H-tetrazol-5-yl)phenyl)quinolin-6-olYield 12%

Reagents, catalysts & solvents 1

HCID 8134Diethylene Glycol Monomethyl EtherSolvent

Procedure

A mixture of 3-chloro-4-(6-hydroxyquinolin-2-yl)benzonitrile (230 mg, 0.819 mmol), NaN3 (55 mg, 0.820 mmol) and LiCl (70 mg, 1.64 mmol) in diethylene glycol monomethyl ether (5 mL) was refluxed for 4 hours. The resulting mixture was cooled, filtered through silica gel pad and purified by prep-HPLC (0.1% TFA as additive) to give Compound IV-23 (32 mg, yield 12%). 1H NMR (CD3OD, 400 MHz): δ 8.52 (d, J=8.4 Hz, 1H), 8.34 (s, 1H), 8.21 (d, J=8.0 Hz, 1H), 8.04 (d, J=9.2 Hz, 1H), 7.92-7.82 (m, 2H), 7.54 (dd, J=9.2, 2.0 Hz, 1H), 7.34 (d, J=2.0 Hz, 1H). MS (ESI): m/z 323.6 [M+H]+.

Workup

  1. temperaturewas refluxed for 4 hours
  2. temperatureThe resulting mixture was cooled
  3. filtrationfiltered through silica gel pad
  4. custompurified by prep-HPLC (0.1% TFA as additive)
  5. customto give Compound IV-23 (32 mg, yield 12%)

Sources & evidence

ORD record
ord-0618580572f346e89125e4fc4ed41284
Source dataset
uspto-grants-2015_12
Patent number
US09221810B2

Reaction notes

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