Sodium Azide → (8-Chloro-2-(2-chlorophenyl)quinolin-3-yl)methanamine

HRID 216748Notes

Reaction equation

HRID 216748 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]=[CH:16][CH:15]=[CH:14][C:13]=1[Cl:18])[C:8]([CH2:19]Cl)=[CH:7]2.[N-:21]=[N+]=[N-].[Na+].CP(C)C>CN(C=O)C.C1COCC1.O>[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]=[CH:16][CH:15]=[CH:14][C:13]=1[Cl:18])[C:8]([CH2:19][NH2:21])=[CH:7]2

Participants

7

Reactant 3

HCID 33557Sodium AzideHCID 68983TrimethylphosphineHCID 592646338-Chloro-3-(chloromethyl)-2-(2-chlorophenyl)quinoline

Product 1

HCID 59264634(8-Chloro-2-(2-chlorophenyl)quinolin-3-yl)methanamine

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Prepared according to Procedure E using 8-chloro-3-(chloromethyl)-2-(2-chloro-phenyl)quinoline (0.685 g, 2.12 mmol) and sodium azide (1.10 g, 17 mmol, 8 eq) in DMF (10 mL). The resulting intermediate was submitted to trimethyl phosphine (1.0M) in THF (2.5 mL, 2.5 mmol, 1.2 eq) in THF (8 mL) and water (2 mL). (8-Chloro-2-(2-chlorophenyl)quinolin-3-yl)methanamine was obtained as a light yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.62 (1H, s), 8.05 (1H, dd, J=8.6, 1.2 Hz), 8.00 (1H, dd, J=7.4, 1.2 Hz), 7.63-7.73 (2H, m), 7.47-7.62 (3H, m), 3.90 (1H, s), 3.75 (1H, s) Mass Spectrum (ESI) m/e=303.1 and 305.0 (M+1)

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-6320683321b3432a9084a3b22c4b2047
Source dataset
uspto-grants-2012_06
Patent number
US08193199B2

Reaction notes

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