Chloroacetyl chloride → 1-(Chloroacetyl)-7-nitro-1,2,3,4-tetrahydroquinoline

HRID 494176Notes

Reaction equation

HRID 494176 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:14][CH2:15][C:16](Cl)=[O:17]>>[Cl:14][CH2:15][C:16]([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:17]

Participants

3

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 2525137-Nitro-1,2,3,4-tetrahydroquinoline

Product 1

HCID 125783601-(Chloroacetyl)-7-nitro-1,2,3,4-tetrahydroquinoline

Procedure

Using the procedure outlined in Description 4, the title compound was prepared from 7-nitro-1,2,3,4-tetrahydroquinoline (D1) (4.41 g, 25 mmol) and chloroacetyl chloride (2.2 ml, 27.6 mmol) as a dark brown solid (5.853 g). 1H NMR (250 MHz, CDCl3) δ (ppm): 8.49 (br, 1H), 8.00 (dd, 1H), 7.33 (d, 1H), 4.27 (s, 2H), 3.86 (m, 2H), 2.90 (t, 2H), 2.09 (m, 2H).

Sources & evidence

ORD record
ord-b4369f1dc49d4eab94db9baee7eb645c
Source dataset
uspto-grants-2009_05
Patent number
US07538121B2

Reaction notes

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