Serinol → 1,3-Propanediol, 2-[(6-methoxy-3-nitro-2-pyridinyl)amino]-

HRID 1943188Notes

Reaction equation

HRID 1943188 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7](Cl)[C:6]([N+:10]([O-:12])=[O:11])=[CH:5][CH:4]=1.[NH2:13][CH:14]([CH2:17][OH:18])[CH2:15][OH:16]>C(O)C>[CH3:1][O:2][C:3]1[N:8]=[C:7]([NH:13][CH:14]([CH2:17][OH:18])[CH2:15][OH:16])[C:6]([N+:10]([O-:12])=[O:11])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 68294SerinolHCID 27950292-Chloro-6-methoxy-3-nitropyridine

Product 1

HCID 221417081,3-Propanediol, 2-[(6-methoxy-3-nitro-2-pyridinyl)amino]-Yield 94.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6-Methoxy-2-chloro-3-nitropyridine (36.94 g, 195.9 mmol) and 2-aminopropane-1,3-diol (35.65 g, 391.3 mmol, 2 eq.) were stirred in ethanol (500 ml) at reflux under argon for 3 hours. The mixture was allowed to cool to room temperature and left overnight. The solvent was partially removed under reduced pressure (to ca. 150 ml) and the resulting bright yellow slurry was poured into ice-water (1.5 L) with vigorous stirring. The mixture was stirred for 1 hour then filtered with suction while cold. The solid was washed with ice-cold water (200 ml) and air-dried to give the title compound as a bright yellow solid (45.03 g, 94%). LCMS showed desired product (93%) plus 7% starting material. The product was used without further purification.

Workup

  1. temperatureat reflux under argon for 3 hours
  2. customThe solvent was partially removed under reduced pressure (to ca. 150 ml)
  3. additionthe resulting bright yellow slurry was poured into ice-water (1.5 L) with vigorous stirring
  4. filtrationthen filtered with suction while cold
  5. washThe solid was washed with ice-cold water (200 ml)
  6. customair-dried

Sources & evidence

ORD record
ord-ec7b86cb1f544ed39ed28ddacef31fca
Source dataset
uspto-grants-2013_03
Patent number
US08389524B2

Reaction notes

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