Morpholine → HCID 22291707, compound

HRID 457306Notes

Reaction equation

HRID 457306 reaction equation
Cl[C:2]1[CH:3]=[C:4]([C:8]([Cl:11])=[CH:9][N:10]=1)[C:5]([OH:7])=[O:6].[NH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1>CN(C)C(=O)C>[Cl:11][C:8]1[C:4]([C:5]([OH:7])=[O:6])=[CH:3][C:2]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[N:10][CH:9]=1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 27360872,5-Dichloroisonicotinic acid

Product 1

HCID 22291707HCID 22291707, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

2,5-Dichloroisonicotinic acid, prepared by the method of E. Marzi, A. Bigi, M. Schlosser, Eur. J. Org. Chem. 2001, 1371–1376, (1.6 g, 0.0083 mol) and morpholine (10.9 g, 0.125 mol) in 4 mL of N,N-dimethylacetamide were heated at 80° C. for 4 days. The volatiles were removed under vacuum and the resulting yellow solid partitioned between water and Et2O. The aqueous layer was acidified to pH=1.5 using an aqueous solution of HCl and extracted once with Et2O (25 mL) and three times with CH2Cl2 (25 mL). The organic extracts were combined and the solvents removed under vacuum. The resulting yellow solid was crystallized from MeOH to afford the title compound 1.07 g (yield: 34%). 1H NMR (300 MHz, d6-DMSO): δ 3.45 (t, 4H, J=4.8 Hz), 3.67 (t, 4H, J=4.8 Hz), 7.06 (s, 1H), 8.21 (s, 1H), 13.79 (s (broad), 1H). 13C HMR (100 MHz, d6-DMSO): δ 45.6, 66.4, 107.3, 116.1, 141.3, 148.3, 158.5, 166.8. M+1=243.

Workup

  1. customThe volatiles were removed under vacuum
  2. customthe resulting yellow solid partitioned between water and Et2O
  3. extractionextracted once with Et2O (25 mL) and three times with CH2Cl2 (25 mL)
  4. customthe solvents removed under vacuum
  5. customThe resulting yellow solid was crystallized from MeOH

Sources & evidence

ORD record
ord-7a7c576eb7a14a11ab6974558a41c225
Source dataset
uspto-grants-2007_03
Patent number
US07186743B2

Reaction notes

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