HCID 73035684, compound → HCID 11680771, compound

HRID 1430341Notes

Reaction equation

HRID 1430341 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C:4]([N:18]=[N+]=[N-])=[CH:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([O:14][CH2:15][CH2:16][Cl:17])[CH:7]=1>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]([C:4]1[NH:18][C:11]2[C:6]([CH:5]=1)=[CH:7][C:8]([O:14][CH2:15][CH2:16][Cl:17])=[C:9]([O:12][CH3:13])[CH:10]=2)=[O:21]

Participants

3

Reactant 1

HCID 73035684HCID 73035684, compound

Product 1

HCID 11680771HCID 11680771, compoundYield 72.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 16 (6.81 g, 21.8 mmol) in toluene (200 mL) was heated at reflux for 4 h. After cooling to room temperature the reaction mixture was concentrated in vacuo. The formed precipitate was isolated by filtration and dried in vacuo to give 17 (4.48 g, 72%) as a pale yellow solid. 1H NMR (300 MHz, DMSO-d6): δ=3.82, 3.84 (2×s, 6 H, OMe, CO2Me), 3.93 (t, J=5.3 Hz, 2 H, 2′-H2), 4.21 (t, J=5.3 Hz, 2 H, 1′-H2), 6.92 (s, 1 H, 7-H), 7.02 (d, J=1.5 Hz, 1 H, 3-H), 7.15 (s, 1 H, 4-H), 11.62 (sbr, 1 H, NH) ppm. —13C NMR (50.3 MHz, DMSO-d6): δ=42.9 (C-2′), 51.3 (CO2Me), 55.5 (OMe), 69.4 (C-1′), 94.8 (C-7), 105.6 (C-4), 107.9 (C-3), 119.7 (C-3a), 125.4 (C-2), 133.2 (C-7a), 144.1 (C-5), 149.8 (C-6), 161.4 (C═O) ppm. −MS (70 eV, EI): m/z (%)=283 (100) [M]+, 220 (50) [M-CH2)2Cl]+. —C13H14ClNO4 (283.71): calcd. C, 55.04; H, 4.97; found C, 54.86; H, 5.06.

Workup

  1. temperatureat reflux for 4 h
  2. concentrationwas concentrated in vacuo
  3. customThe formed precipitate was isolated by filtration
  4. customdried in vacuo

Sources & evidence

ORD record
ord-ae4282431f4347e4b4c9110a8ea90832
Source dataset
uspto-grants-2015_01
Patent number
US08940784B2

Reaction notes

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