4-tert-Butylbenzoic acid → Benzoic acid, 4-(1,1-dimethylethyl)-, hydrazide

HRID 393828

Reaction equation

HRID 393828 reaction equation
[C:1]([C:5]1[CH:13]=[CH:12][C:8]([C:9](O)=[O:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].CN1CCOCC1.ClC(OCC(C)C)=O.[NH2:29][NH2:30]>C(OCC)(=O)C>[C:1]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([NH:29][NH2:30])=[O:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 74034-tert-Butylbenzoic acidHCID 79724-MethylmorpholineHCID 9321HydrazineHCID 62365Isobutyl chloroformate

Product 1

HCID 123513Benzoic acid, 4-(1,1-dimethylethyl)-, hydrazide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 4-tert-butyl benzoic acid (0.2 g, 1.2 mmol in 10 mL of dry THF) cooled to 0° C. and treated with N-methyl-morpholine (1.6 mL, 14.6 mmol) as well as isobutyl chloroformate (1.7 mL, 1.3 mmol). Then the mixture was stirred for 10 minutes at 0° C. After hydrazine (0.6 g, 3.6 mmol) was added to the reaction mixture, it was stirred 3 hours at 25° C. The reaction was then diluted with ethyl acetate (100 mL), washed with saturated sodium bicarbonate solution as well as brine, and concentrated in vacuum. The crude material was chromatographed on silica gel eluting with hexanes/ethyl acetate=2:1 to give 4-tert-butyl-benzoic acid hydrazide.

Workup

  1. stirringwas stirred 3 hours at 25° C
  2. washwashed with saturated sodium bicarbonate solution as well as brine
  3. concentrationconcentrated in vacuum
  4. customThe crude material was chromatographed on silica gel eluting with hexanes/ethyl acetate=2:1

Sources & evidence

ORD record
ord-f8af978295af440990998aaf3a31624f
Source dataset
uspto-grants-2004_10
Patent number
US06809119B2

Linked notes

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