Sodium Hydroxide → N'-tert-butyl-3-methoxy-2-methylbenzohydrazide

HRID 260808Notes

Reaction equation

HRID 260808 reaction equation
Cl.[C:2]([NH:6][NH2:7])([CH3:5])([CH3:4])[CH3:3].[OH-].[Na+].[CH3:10][O:11][C:12]1[C:13]([CH3:21])=[C:14]([CH:18]=[CH:19][CH:20]=1)[C:15](Cl)=[O:16]>C(Cl)Cl.O>[CH3:10][O:11][C:12]1[C:13]([CH3:21])=[C:14]([CH:18]=[CH:19][CH:20]=1)[C:15]([NH:7][NH:6][C:2]([CH3:5])([CH3:4])[CH3:3])=[O:16]

Participants

6

Reactant 3

HCID 14798Sodium Hydroxide2×HCID 81889tert-Butylhydrazine monohydrochlorideHCID 14719554Benzoyl chloride, 3-methoxy-2-methyl-

Product 1

HCID 15376235N'-tert-butyl-3-methoxy-2-methylbenzohydrazideYield 96%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred suspension of tert-butylhydrazine hydrochloride (397 g, 3.27 mole) in methylene chloride (2 L) at 0° C., was added sodium hydroxide (50% aqueous, 260 g) diluted with water (400 mL). Following this, 3-methoxy-2-methylbenzoyl chloride (140 g, 0.78 mole) in methylene chloride (1 L) and sodium hydroxide (50% aqueous, 80 g) dilutect with water (400 mL) were added concurrently at -20° C. After the addition was complete, the reaction mixture was allowed to warm to room temperature and after additional 30 minutes, the organic layer was washed with water (4×500 mL), dried over magnesium sulfate and stripped to yield N-(3-methoxy-2-methylbenzoyl)-N'-tert-butylhydrazine (177 g). 1H-NMR (CDCl3) δppm 1.19 (s, 9H, t-Bu), 2.29 (s, 3H, CH3), 3.87 (s, 3H, OCH3), 6.90 (d, 1H, C-4 or 6 ), 6.95 (d, 1H, C-4 or C6) 7.19 (dd, 1H, C-5).

Workup

  1. additionwere added concurrently at -20° C
  2. additionAfter the addition
  3. washthe organic layer was washed with water (4×500 mL)
  4. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-e22d6a256a3a4510a0e8e1f40b074299
Source dataset
uspto-grants-1996_06
Patent number
US05530028

Reaction notes

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