1,2-Dimethoxyethane → N-(6-nitro-2,3-dihydro-1H-inden-5-yl)acetamide

HRID 1669036Notes

Reaction equation

HRID 1669036 reaction equation
ClC1N=[N+:4]([O-:15])[C:5]2[CH:14]=[C:13]3[C:9]([CH2:10][CH2:11][CH2:12]3)=[CH:8][C:6]=2[N:7]=1.[O:16]1CCCN(CCN)CC1.CCN(CC)CC.C[O:34][CH2:35][CH2:36]OC>>[N+:4]([C:5]1[CH:14]=[C:13]2[C:9]([CH2:10][CH2:11][CH2:12]2)=[CH:8][C:6]=1[NH:7][C:35](=[O:34])[CH3:36])([O-:15])=[O:16]

Participants

5

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 8471TriethylamineHCID 160813203-Chloro-7,8-dihydro-6H-indeno[5,6-e][1,2,4]triazine 1-OxideHCID 57640201878155-50-1

Product 1

HCID 10751392N-(6-nitro-2,3-dihydro-1H-inden-5-yl)acetamide

Conditions

Temperature
20 °C

Procedure

A solution of chloride 21 (2.0 g, 9.0 mmol), 2-(1,4-oxazepan-4-yl)ethylamine (292) (1.63 g, 11.3 mmol) and Et3N (1.3 mL, 9.9 mmol) in DME (140 mL) was stirred at reflux temperature for 20 h. The solution was cooled to 20° C., the solvent evaporated and the residue purified by column chromatography, eluting with a gradient (2-6%) of MeOH/DCM, to give (i) starting material 21 (0.5 g, 25%) and (ii) 1-oxide 48 (1.24 g, 42%) as a yellow solid: mp 119-120° C.; 1H NMR δ 8.08 (s, 1H, H-9), 7.40 (s, 1H, H-5), 5.82 (br s, 1H, NH), 3.81 (t, J=6.1 Hz, 2H, CH2O), 3.74 (t, J=4.7 Hz, 2H, CH2), 3.51-3.56 (m, 2H, CH2), 2.97-3.04 (m, 4H, H-6, H-8), 2.73-2.80 (m, 6H, 3×CH2), 2.15 (p, J=7.4 Hz, 2H, H-7), 1.88-1.94 (m, 2H, CH2); 13C NMR δ 158.7, 154.6, 148.8, 143.3, 129.8, 120.5, 114.7, 69.3, 68.7, 57.5, 55.8, 53.6, 38.7, 33.1, 32.3, 30.0, 25.7; HRMS (FAB+) calcd for C17H24N5O2 (MH+) m/z 330.1930, found 330.1937.

Workup

  1. temperatureat reflux temperature for 20 h
  2. customthe solvent evaporated
  3. customthe residue purified by column chromatography
  4. washeluting with a gradient (2-6%) of MeOH/DCM

Sources & evidence

ORD record
ord-02dbff65ee5d4b2f899326a1931d3a5e
Source dataset
uspto-grants-2011_08
Patent number
US07989451B2

Reaction notes

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