Morpholine → HCID 22291707、化合物

HRID 457306ノート

反応式

HRID 457306 の反応式
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

参加物

4

反応物 2

HCID 8083MorpholineHCID 27360872,5-dichloropyridine-4-carboxylic Acid

生成物 1

HCID 22291707HCID 22291707、化合物収率 34%

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-7a7c576eb7a14a11ab6974558a41c225
出典データセット
uspto-grants-2007_03
特許番号
US07186743B2

反応ノート

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