Diisopropylamine → 1-(2-Diisopropylaminoacetyl)-7-nitro-1,2,3,4-tetrahydroquinoline

HRID 494177Notes

Reaction equation

HRID 494177 reaction equation
Cl[CH2:2][C:3]([N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([N+:15]([O-:17])=[O:16])[CH:13]=2)[CH2:8][CH2:7][CH2:6]1)=[O:4].[CH:18]([NH:21][CH:22]([CH3:24])[CH3:23])([CH3:20])[CH3:19]>C1COCC1>[CH:18]([N:21]([CH:22]([CH3:24])[CH3:23])[CH2:2][C:3]([N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([N+:15]([O-:17])=[O:16])[CH:13]=2)[CH2:8][CH2:7][CH2:6]1)=[O:4])([CH3:20])[CH3:19]

Participants

4

Reactant 2

HCID 7912DiisopropylamineHCID 125783601-(Chloroacetyl)-7-nitro-1,2,3,4-tetrahydroquinoline

Product 1

HCID 690387001-(2-Diisopropylaminoacetyl)-7-nitro-1,2,3,4-tetrahydroquinoline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-(2-chloroacetyl)-7-nitro-1,2,3,4-tetrahydroquinoline (D8) (6.7 g, 26 mmol) and diisopropylamine (50 ml) in THF (50 ml) was heated at reflux for 5d then cooled to room temperature. Aqueous work-up yielded a crude oil which was purified by flash column chromatography. Elution with 0-5% methanol/DCM gave the title compound as a dark oil (6.56 g). 1H NMR (250 MHz, CDCl3) δ (ppm): 8.62 (br, 1H), 7.91 (dd, 1H), 7.27 (d, 1H), 3.95 (m, 2H), 3.54 (s, 2H), 3.02 (sp, 2H), 2.87 (t, 2H), 2.02 (m, 2H), 1.02 (d, 12H).

Workup

  1. temperaturewas heated
  2. customAqueous work-up yielded a crude oil which
  3. customwas purified by flash column chromatography
  4. washElution with 0-5% methanol/DCM

Sources & evidence

ORD record
ord-be82e23557fa4c80b1a64702cdd87117
Source dataset
uspto-grants-2009_05
Patent number
US07538121B2

Reaction notes

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