Clopyralid → HCID 22291830, compound

HRID 968105Notes

Reaction equation

HRID 968105 reaction equation
[Cl:1][C:2]1[C:3]([C:9]([OH:11])=O)=[N:4][C:5]([Cl:8])=[CH:6][CH:7]=1.[NH2:12][C:13]1[CH:37]=[CH:36][C:16]2[CH2:17][CH2:18][C:19]3[C:20]([C:33]([NH2:35])=[O:34])=[N:21][N:22]([C:24]4[CH:32]=[CH:31][C:27]5[O:28][CH2:29][O:30][C:26]=5[CH:25]=4)[C:23]=3[C:15]=2[CH:14]=1>>[O:28]1[C:27]2[CH:31]=[CH:32][C:24]([N:22]3[C:23]4[C:15]5[CH:14]=[C:13]([NH:12][C:9]([C:3]6[C:2]([Cl:1])=[CH:7][CH:6]=[C:5]([Cl:8])[N:4]=6)=[O:11])[CH:37]=[CH:36][C:16]=5[CH2:17][CH2:18][C:19]=4[C:20]([C:33]([NH2:35])=[O:34])=[N:21]3)=[CH:25][C:26]=2[O:30][CH2:29]1

Participants

3

Reactant 2

HCID 15553ClopyralidHCID 22291565HCID 22291565, compound

Product 1

HCID 22291830HCID 22291830, compound

Procedure

The title compound was synthesized from 1.653 g of 3,6-dichloro-2-pyridine carboxylic acid (CP92740, prepared by the method of E. Marzi, A. Bigi, M. Schlosser, Eur. J. Org. Chem. 2001, 1371-1376) and the title compound of step 4 of Example 161 (2.0 g) by the same procedure used for Example 211. The title compound is a brown solid (2.4 g, 80%), m.p. 263-265° C. Its structure was confirmed by 1H NMR and LC/MS: 1H NMR (d6-DMSO): δ 2.82-3.01 (m, 4H)), 6.11 (s, 2H), 6.97-7.07 (m, 2H), 7.38 d, 1H, J=1 Hz), 7.81 (s, 1H), 7.33-7.42 (m, 3H), 7.52 (s, 1H), 7.51 (d, 1H, J=9 Hz), 8.15 (d, 1H, J=9 Hz), 10.57 (s, 1H). ESI mass spectrum for C25H18Cl2N5O4+: 522 (M+1).

Workup

  1. customprepared by the method of E
  2. custom6.11 (s, 2H), 6.97-7.07 (m, 2H), 7.38 d, 1H, J=1 Hz

Sources & evidence

ORD record
ord-0d643f0083824982a8fba162dc172414
Source dataset
uspto-grants-2005_10
Patent number
US06956052B2

Reaction notes

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