Ammonia → 4-Hydroxy-3,5-dimethoxy-benzoic acid N-tert-butyl-N'-(5-methyl-2,3-dihydro-benzo[1,4]dioxine-6-carbonyl)-hydrazide

HRID 39641Notes

Reaction equation

HRID 39641 reaction equation
[C:1]([N:5]([C:20]([C:22]1[CH:27]=[C:26]([O:28][CH3:29])[C:25]([O:30]C(=O)C)=[C:24]([O:34][CH3:35])[CH:23]=1)=[O:21])[NH:6][C:7]([C:9]1[CH:18]=[CH:17][C:12]2[O:13][CH2:14][CH2:15][O:16][C:11]=2[C:10]=1[CH3:19])=[O:8])([CH3:4])([CH3:3])[CH3:2].N>CO>[C:1]([N:5]([C:20](=[O:21])[C:22]1[CH:27]=[C:26]([O:28][CH3:29])[C:25]([OH:30])=[C:24]([O:34][CH3:35])[CH:23]=1)[NH:6][C:7]([C:9]1[CH:18]=[CH:17][C:12]2[O:13][CH2:14][CH2:15][O:16][C:11]=2[C:10]=1[CH3:19])=[O:8])([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 59838636Acetic acid 4-[N-tert-butyl-N'-(5-methyl-2,3-dihydro-benzo[1,4]dioxine-6-carbonyl)-hydrazinocarbonyl]-2,6-dimethoxy-phenyl ester

Product 1

HCID 598386484-Hydroxy-3,5-dimethoxy-benzoic acid N-tert-butyl-N'-(5-methyl-2,3-dihydro-benzo[1,4]dioxine-6-carbonyl)-hydrazideYield 40.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Acetic acid 4-[N-tert-butyl-N′-(5-methyl-2,3-dihydro-benzo[1,4]dioxine-6-carbonyl)-hydrazinocarbonyl]-2,6-dimethoxy-phenyl ester (300 mg) was dissolved in methanol with 28% aqueous ammonia (750 mg). The mixture was stirred at ambient temperature over the weekend. The precipitate was filtered to provide 110 mg of white solid 4-hydroxy-3,5-dimethoxy-benzoic acid N-tert-butyl-N′-(5-methyl-2,3-dihydro-benzo[1,4]dioxine-6-carbonyl)-hydrazide. 1H NMR (CDCl3, 300 MHz) δ (ppm): 1.59 (s, 15H), 2.02 (s, 3H), 3.85 (s, 6H), 4.21 (m, 4H), 5.6-5.7 (broad s, 1H), 6.22 (d, 1H), 6.58 (d, 1H), 6.81 (s, 2H).

Workup

  1. filtrationThe precipitate was filtered

Sources & evidence

ORD record
ord-ef012be4a0304d1191c765f2e216af0d
Source dataset
uspto-grants-2013_09
Patent number
US08524948B2

Reaction notes

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