Hydrazine hydrate (1:1) → 3-Cyano-4-[(1-methylethyl)oxy]benzohydrazide

HRID 222930Notes

Reaction equation

HRID 222930 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[O:12][CH:13]([CH3:15])[CH3:14])[C:6](O)=[O:7])#[N:2].C(N1C=CN=C1)(N1C=CN=C1)=O.O.[NH2:29][NH2:30]>O1CCCC1>[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[O:12][CH:13]([CH3:15])[CH3:14])[C:6]([NH:29][NH2:30])=[O:7])#[N:2]

Participants

5

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 682631,1'-CarbonyldiimidazoleHCID 21956832RP-101124

Product 1

HCID 575942713-Cyano-4-[(1-methylethyl)oxy]benzohydrazideYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-cyano-4-[(1-methylethyl)oxy]benzoic acid (0.300 g, 1.46 mmol) in tetrahydrofuran (10.0 mL) was treated with 1,1′-carbonyldiimidazole (0.261 g, 1.61 mmol). After stirring 2 h at ambient temperature, hydrazine monohydrate (0.213 mL, 4.39 mmol) was added. After stirring an additional 2 h at ambient temperature, the reaction mixture was concentrated in vacuo. Purification via flash column chromatography (0-5% MeOH/EtOAc) gave the title compound as a white solid (0.304 g; 95%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 8.51 (br. s., 1H) 8.06 (d, J=2.3 Hz, 1H) 8.02 (dd, J=8.8, 2.3 Hz, 1H) 7.00 (d, J=8.8 Hz, 1H) 5.15 (br. s., 2H) 4.71 (qq, J=6.1 Hz, 1H) 1.40 (d, J=6.1 Hz, 6H). MS (ES+) m/e 220 [M+H]+.

Workup

  1. stirringAfter stirring an additional 2 h at ambient temperature
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. customPurification via flash column chromatography (0-5% MeOH/EtOAc)

Sources & evidence

ORD record
ord-2babfbdc71614ff3b44e5533858157d8
Source dataset
uspto-grants-2012_06
Patent number
US08207340B2

Reaction notes

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