Ethanolamine → HC Yellow no. 12

HRID 558182Notes

Reaction equation

HRID 558182 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[NH2:12][CH2:13][CH2:14][OH:15]>C(O)CCC>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]([NH:12][CH2:13][CH2:14][OH:15])=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=1

Participants

4

Reactant 2

HCID 700EthanolamineHCID 69772,5-Dichloronitrobenzene

Product 1

HCID 5182864HC Yellow no. 12Yield 86%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 1,4-dichloro-2-nitrobenzene (I-1, Aldrich, Wis.; 38.4 g, 0.2 mol) and 2-aminoethanol (24.4 g, 0.4 mol, 2 eq.) in n-butanol (100 mL) was refluxed overnight. The solvent was evaporated and the residue was dispersed in petrol ether (600 mL) and stirred overnight. The solids were filtered to give intermediate I-2 as a yellow powder (37 g, 86%). 1H-NMR (400 MHz, CDCl3): δ 8.24 (s, 1H), 8.19˜8.20 (d, 1H, J=2.4 Hz), 7.39˜7.42 (dd, 1H, J1=2.4 Hz, J2=9.2 Hz), 6.87˜6.90 (d, 1H, J=9.6 Hz), 3.95˜3.98 (t, 2H, J=5.2 Hz), 3.49˜3.53 (dd, 2H, J1=4.8 Hz, J2=10.4 Hz). MS (ESI): m/z 217 (M+H+).

Workup

  1. temperaturewas refluxed overnight
  2. customThe solvent was evaporated
  3. additionthe residue was dispersed in petrol ether (600 mL)
  4. filtrationThe solids were filtered

Sources & evidence

ORD record
ord-fda71cc00bfa40cc88e2a1bf3413119e
Source dataset
uspto-grants-2011_11
Patent number
US08063032B2

Reaction notes

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