Methanol → HCID 68945666, compound

HRID 1508025Notes

Reaction equation

HRID 1508025 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1.[OH:13][S:14]([OH:17])(=[O:16])=[O:15].[CH3:18]O>>[S:14](=[O:15])(=[O:13])([OH:17])[OH:16].[CH3:18][O:11][C:10](=[O:12])[CH2:9][CH2:8][C:5]1[CH:4]=[CH:3][C:2]([NH2:1])=[CH:7][CH:6]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 754513-(4-Aminophenyl)propionic acid

Product 1

HCID 68945666HCID 68945666, compoundYield 85%

Conditions

Temperature
45 °C

Procedure

To a mixture of 3-(4-amino-phenyl)-propionic acid (1.00 g, 6.05 mmol) in 10 mL of methyl alcohol (MeOH) was added 0.80 mL of conc H2SO4. The resulting mixture was refluxed for 2 h, concentrated down to ca. half volume by distillation and then cooled to 45° C. Methyl tert-butyl ether (MTBE, 15 mL) was added. The mixture was allowed to cool to 0° C. and stirred for 0.5 h. The solid was collected by filtration and washed with 1:4 MeOH/MTBE (2×10 mL), MTBE (3×10 mL) and dried under reduced pressure. The title compound (1.43 g, 85%) was obtained as a white solid. 1H-NMR (DMSO-d6; 400 MHz): δ 8.40-11.0 (br s, 4H), 7.34 (d, 2H, J=8.2 Hz), 7.23 (d, 2H, J=8.2 Hz), 3.57 (s, 3H), 2.86 (t, 2H, J=7.4 Hz), 2.64 (t, 2H, J=7.4 Hz).

Workup

  1. temperatureThe resulting mixture was refluxed for 2 h
  2. concentrationconcentrated down to ca. half volume by distillation
  3. additionMethyl tert-butyl ether (MTBE, 15 mL) was added
  4. temperatureto cool to 0° C.
  5. filtrationThe solid was collected by filtration
  6. washwashed with 1:4 MeOH/MTBE (2×10 mL), MTBE (3×10 mL)
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-bc98994cd2414aeebab834a451abf176
Source dataset
uspto-grants-2015_12
Patent number
US09221797B2

Reaction notes

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