Ethanolamine → 2-[(1-Oxido-7,8-dihydro-6H-indeno[5,6-e][1,2,4]triazin-3-yl)amino]ethanol

HRID 1669012Notes

Reaction equation

HRID 1669012 reaction equation
[NH2:1][CH2:2][CH2:3][OH:4].Cl[C:6]1[N:7]=[N+:8]([O-:19])[C:9]2[CH:18]=[C:17]3[C:13]([CH2:14][CH2:15][CH2:16]3)=[CH:12][C:10]=2[N:11]=1>COCCOC>[O-:19][N+:8]1[C:9]2[CH:18]=[C:17]3[C:13](=[CH:12][C:10]=2[N:11]=[C:6]([NH:1][CH2:2][CH2:3][OH:4])[N:7]=1)[CH2:14][CH2:15][CH2:16]3

Participants

4

Reactant 2

HCID 700EthanolamineHCID 160813203-Chloro-7,8-dihydro-6H-indeno[5,6-e][1,2,4]triazine 1-Oxide

Product 1

HCID 119507602-[(1-Oxido-7,8-dihydro-6H-indeno[5,6-e][1,2,4]triazin-3-yl)amino]ethanolYield 99.1%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

2-Aminoethanol (1.80 mL, 30.0 mmol) was added to a stirred solution of chloride 21 (2.21 g, 10.0 mmol) in DME (100 mL) and the solution stirred at reflux temperature for 90 min. The solvent was evaporated and the residue stirred with water (150 mL) at 20° C. for 30 min. The solid was filtered, washed with water several times and dried to give alcohol 24 (2.44 g, 99%) as an orange solid: mp (DME/water) 222-224° C.; 1H NMR [(CD3)2SO] δ 7.92 (s, 1H, H-9), 7.54 (br t, J=6.0 Hz, 1H, NH), 7.36 (s, 1H, H-5), 4.68 (t, J=6.0 Hz, 1H, OH)), 3.56 (q, J=6.0 Hz, 2H, CH2O), 3.40 (q, J=6.0 Hz, 2H, CH2N), 2.89-3.00 (m, 4H, H-6, H-8), 2.00-2.08 (m, 2H, H-7); 13C NMR [(CD3)2SO] δ 158.7, 154.0 148.0, 142.3, 128.8, 120.0, 113.9, 59.3, 43.2, 32.4, 31.6, 25.2. Anal. calcd for C12H14N4O2: C, 58.5; H, 5.7; N, 22.8. Found: C, 58.8; H, 5.9; N, 22.9%.

Workup

  1. temperatureat reflux temperature for 90 min
  2. customThe solvent was evaporated
  3. stirringthe residue stirred with water (150 mL) at 20° C. for 30 min
  4. filtrationThe solid was filtered
  5. washwashed with water several times
  6. customdried

Sources & evidence

ORD record
ord-75e920e3cbab44c8b5468d6c26dfe2c8
Source dataset
uspto-grants-2011_08
Patent number
US07989451B2

Reaction notes

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