Hydrazine hydrate (1:1) → Butanoic acid, 2-hydroxy-2-(trifluoromethyl)-, hydrazide

HRID 1988207Notes

Reaction equation

HRID 1988207 reaction equation
[OH:1][C:2]([C:10]([F:13])([F:12])[F:11])([CH2:8][CH3:9])[C:3](OCC)=[O:4].O.[NH2:15][NH2:16]>>[OH:1][C:2]([C:10]([F:13])([F:12])[F:11])([CH2:8][CH3:9])[C:3]([NH:15][NH2:16])=[O:4]

Participants

3

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 57437841Butanoic acid, 2-hydroxy-2-(trifluoromethyl)-, ethyl ester

Product 1

HCID 57729255Butanoic acid, 2-hydroxy-2-(trifluoromethyl)-, hydrazide

Procedure

The ethyl ester of step 1 (50.04 g, 250 mmol) and hydrazine hydrate (25.03 g, 50 mmol) were heated at 80° C. for 18 h. The excess hydrazine was removed under vacuum and the crude product was filtered through a pad of silica gel with EtOAc-Hexane (ca. 3 L) to furnish the title compound. 1H NMR (400 MHz, acetone-d6): δ 9.7 (s, 1H), 6.10 (s, 1H), 2.25 (m, 1H), 1.85 (m, 1H) and 0.95 t, (3H).

Workup

  1. customThe excess hydrazine was removed under vacuum
  2. filtrationthe crude product was filtered through a pad of silica gel with EtOAc-Hexane (ca. 3 L)

Sources & evidence

ORD record
ord-90fe599131874dc3ae92e8fb92055256
Source dataset
uspto-grants-2009_06
Patent number
US07553973B2

Reaction notes

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