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Thionyl Chloride → 3-(Azidomethyl)-8-chloro-2-(5-fluoro-2-methoxyphenyl)quinoline

HRID 216825
Notes
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Reaction equation

HRID 216825 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]1[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=1[O:19][CH3:20])[C:8]([CH:21]=O)=[CH:7]2.[BH4-].[Na+].S(Cl)(Cl)=O.[N-:29]=[N+:30]=[N-:31].[Na+]>C1COCC1.O.C(Cl)(Cl)Cl>[N:29]([CH2:21][C:8]1[C:9]([C:12]2[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=2[O:19][CH3:20])=[N:10][C:11]2[C:6]([CH:7]=1)=[CH:5][CH:4]=[CH:3][C:2]=2[Cl:1])=[N+:30]=[N-:31]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 24386Thionyl ChlorideHCID 33557Sodium AzideHCID 4311764Sodium borohydrideHCID 577079228-Chloro-2-(5-fluoro-2-methoxyphenyl)quinoline-3-carbaldehyde

Product 1

HCID 577079883-(Azidomethyl)-8-chloro-2-(5-fluoro-2-methoxyphenyl)quinoline

Reagents, catalysts & solvents 3

HCID 962
Water
Solvent
2×
HCID 6212ChloroformSolvent
HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 8-chloro-2-(5-fluoro-2-methoxyphenyl)quinoline-3-carbaldehyde (385.4 mg, 1.221 mmol) in THF (6.0 mL) was added sodium borohydride (1.831 mmol) at rt. The solution was stirred 1 hour then diluted with water, and extracted with EtOAc to provide a crude solid after solvent removal, which was used without further purification. To the crude alcohol in CHCl3 (6 mL) was added thionyl chloride (0.445 mL, 6.103 mmol) at r.t. and stirred overnight. After 14 h the solvents were removed (TLC indicates complete.) The solid was dissolved in DMF (6 mL) then sodium azide (2.441 mmol) was added at once, and stirred 1 hour, poured into water and extracted EtOAc to give a crude material: 373.3 mg Chromatography, gradient 89/9/1. 1H NMR (400 MHz, choroform-d) δ ppm 8.28 (1H, s), 7.86 (1H, dd, J=7.4, 1.4 Hz), 7.83 (1H, dd, J=8.2, 1.4 Hz), 7.51 (1H, dd, J=8.1, 7.5 Hz), 7.22 (1H, dd, J=8.2, 3.1 Hz), 7.13-7.19 (1H, m), 6.95 (1H, dd, J=9.0, 4.3 Hz), 4.48 (2H, s), 3.76 (3H, s) Mass Spectrum (ESI) m/e=343.1 (M+1).

Workup

  1. extractionextracted with EtOAc
  2. customto provide a crude solid
  3. customafter solvent removal, which
  4. customwas used without further purification
  5. stirringstirred overnight
  6. customAfter 14 h the solvents were removed (TLC indicates complete.) The solid
  7. dissolutionwas dissolved in DMF (6 mL)
  8. stirringstirred 1 hour
  9. extractionextracted EtOAc

Sources & evidence

ORD record
ord-73a0d2e38e5645a381c402123b12f4e0
Source dataset
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08193199B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes