Hydrazine hydrate (1:1) → HCID 86729586, compound

HRID 574233Notes

Reaction equation

HRID 574233 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[C:10]([C:21](OC)=[O:22])=[N:11][C:12]([O:19][CH3:20])=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.[NH2:26][NH2:27]>CO.O>[NH:26]([C:21]([C:10]1[C:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[CH:14][C:13]([C:15]([F:18])([F:16])[F:17])=[C:12]([O:19][CH3:20])[N:11]=1)=[O:22])[NH2:27]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86729606HCID 86729606, compound

Product 1

HCID 86729586HCID 86729586, compoundYield 97.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A suspension of methyl 3-(tert-butoxycarbonylamino)-6-methoxy-5-(trifluoromethyl)picolinate (step 2) (3.1 g, 8.85 mmol) in dry MeOH (20 ml) was treated with hydrazine monohydrate (1.108 g, 22.12 mmol) and the suspension was heated at reflux overnight. The mixture was diluted with water and the resulting precipitate was collected by filtration and dried in a vacuum oven to afford the title compound as a light brown solid (3.01 g). LC-MS Rt=1.27 min [M+H]+ 251 [−minus Boc group] (Method HighpH_v003.).

Workup

  1. temperaturethe suspension was heated
  2. temperatureat reflux overnight
  3. filtrationthe resulting precipitate was collected by filtration
  4. customdried in a vacuum oven

Sources & evidence

ORD record
ord-6b4d0c291b2c4fab85ad3b746fe50f8d
Source dataset
uspto-grants-2015_05
Patent number
US09034879B2

Reaction notes

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