Hydrochloric Acid → HCID 89647663, compound

HRID 1399783Notes

Reaction equation

HRID 1399783 reaction equation
Cl[C:2]1[CH:3]=[C:4]([C:8]([N+:11]([O-:13])=[O:12])=[CH:9][N:10]=1)[C:5]([OH:7])=[O:6].[NH:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1.Cl>O>[O:17]1[CH2:18][CH2:19][N:14]([C:2]2[CH:3]=[C:4]([C:8]([N+:11]([O-:13])=[O:12])=[CH:9][N:10]=2)[C:5]([OH:7])=[O:6])[CH2:15][CH2:16]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8083MorpholineHCID 184406222-Chloro-5-nitroisonicotinic acid

Product 1

HCID 89647663HCID 89647663, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-chloro-5-nitroisonicotinic acid (28.5 g, 141 mmol), morpholine (36.8 g, 423 mmol) and k2CO3 (58.4 g, 423 mmol) was stirred at 100° C. for 4 h. The mixture was cooled to room temperature and poured into water (1.5 L). It was acidified with 4N HCl to pH=1 and extracted with EA (1 L×3). The combined organic layers were washed with brine (1 L×5), then dried over anhydrous Na2SO4, filtered and concentrated in vacuo to afford the desired product as a yellow solid (27 g, 76%); LC/MS: MS (ES+) m/e 254 (MH+); 1H NMR (300 MHz, DMSO-d6) δ ppm 3.68 (t, J=4.8 Hz, 1H), 3.77 (t, J=4.8 Hz, 4H), 6.99 (s, 1H), 8.91 (s, 1H).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. extractionextracted with EA (1 L×3)
  3. washThe combined organic layers were washed with brine (1 L×5)
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bbed65a0e7f24bc7bbe101e214813d7f
Source dataset
uspto-grants-2014_12
Patent number
US08906910B2

Reaction notes

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