Benzylamine → HCID 178516089, compound

HRID 2050339Notes

Reaction equation

HRID 2050339 reaction equation
Cl[C:2]1[N:7]=[C:6]([OH:8])[CH:5]=[CH:4][CH:3]=1.[CH2:9]([NH2:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(O)C>[CH2:9]([NH:16][C:2]1[N:7]=[C:6]([OH:8])[CH:5]=[CH:4][CH:3]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 1785160256-chloropyridin-2-ol

Product 1

HCID 178516089HCID 178516089, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
25 °C

Procedure

6-Chloro-2-pyridinol (6.1 g, 0.047 mole) and 10.1 g (0.094 mole) of benzylamine were mixed and heated in an oil bath at 120°-130° for 48 hours. The liquid mass gradually solidified. The cooled mixture was boiled with 100 ml of 50% aqueous ethanol and cooled to 25° C.; the supernatant was decanted from a gum (which was saved), cooled to 5° C., decanted from black tar, and diluted with 50 ml of water. A grey, granular solid, m.p. 158°-162° C., crystallized. An additional quantity of the same material was recovered as follows: The retained gum was digested with 50 ml of hot 95% ethanol until it was solid; the mixture was cooled to 5° C., the solid removed, and the filtrate diluted with water. The total yield of the title compound was 2.4 g (25%). Recrystallization from benzene-n-hexane raised the m.p. to 164°-165°. 1H nmr (CDCl3 +D2O, 100 MHz), δ4.28 (s, 2H, CH2), 5.28 (d, 1H, H5, J=8 Hz), 5.50 (d, 1H, H3, J=9 Hz), 7.17 (t, 1H, H4, J=8 Hz), 7.30 (s, 5H, C6H5).

Workup

  1. temperatureheated in an oil bath at 120°-130° for 48 hours
  2. customthe supernatant was decanted from a gum (which was saved)
  3. temperaturecooled to 5° C.
  4. customdecanted from black tar
  5. additiondiluted with 50 ml of water
  6. customA grey, granular solid, m.p. 158°-162° C., crystallized
  7. customAn additional quantity of the same material was recovered
  8. temperaturethe mixture was cooled to 5° C.
  9. customthe solid removed
  10. additionthe filtrate diluted with water
  11. customRecrystallization from benzene-n-hexane
  12. temperatureraised the m.p. to 164°-165°

Sources & evidence

ORD record
ord-f2b6edf593c848e4a01a29921c71412f
Source dataset
uspto-grants-1980_04
Patent number
US04200753

Reaction notes

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