7-Nitro-1,2,3,4-tetrahydroquinoline → HCID 56978694, compound

HRID 494175Notes

Reaction equation

HRID 494175 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][NH:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl.[CH3:15][N:16]([CH2:18][C:19](Cl)=[O:20])[CH3:17]>>[CH3:15][N:16]([CH3:17])[CH2:18][C:19]([N:11]1[C:12]2[C:7](=[CH:6][CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:13]=2)[CH2:8][CH2:9][CH2:10]1)=[O:20]

Participants

3

Reactant 2

HCID 2525137-Nitro-1,2,3,4-tetrahydroquinolineHCID 139949912-(Dimethylamino)acetyl chloride hydrochloride

Product 1

HCID 56978694HCID 56978694, compound

Procedure

Using the procedure outlined in Description 4 followed by silica SPE chromatography eluting with 20% EtOAc/MeOH the title compound was prepared from 7-nitro-1,2,3,4-tetrahydroquinoline (D1) (178 mg, 1 mmol) and dimethylaminoacetyl chloride hydrochloride (174 mg, 1.1 mmol) as a yellow solid (103 mg). 1H NMR (250 MHz, CDCl3) δ (ppm): 8.74 (d, 1H), 7.92 (dd, 1H), 7.28 (d, 1H), 3.87 (m, 2H), 3.25 (s, 2H), 2.87 (t, 2H), 2.35 (s, 6H), 1.95 (m, 2H).

Workup

  1. washeluting with 20% EtOAc/MeOH the title compound

Sources & evidence

ORD record
ord-78ef6847a0664fde9b0aeb2bf20960be
Source dataset
uspto-grants-2009_05
Patent number
US07538121B2

Reaction notes

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