Methanol → HCID 644030, compound

HRID 1667551Notes

Reaction equation

B(Br)(Br)Br.[CH2:5]([N:7]([CH2:35][CH3:36])[C:8]1[CH:34]=[CH:33][C:11]([CH:12]=[N:13][N:14](CC2C=CC(C)=CC=2)[C:15](=[O:24])[C:16]2[CH:21]=[CH:20][C:19]([O:22]C)=[CH:18][CH:17]=2)=[CH:10][CH:9]=1)[CH3:6].CO>C(Cl)Cl>[CH2:35]([N:7]([CH2:5][CH3:6])[C:8]1[CH:9]=[CH:10][C:11]([CH:12]=[N:13][NH:14][C:15](=[O:24])[C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=2)=[CH:33][CH:34]=1)[CH3:36]

Participants

Conditions

Temperature: 0 °C

Procedure

BBr3 (2 mL, 1.0 M solution in dichloromethane) was added dropwise to a cooled (0° C.) solution of 4-Methoxy-benzoic acid N′-(4-diethylamino-benzylidene)-N-(4-methyl-benzyl)-hydrazide (compound 2) (0.33 g, 0.00077 mol) in dried CH2Cl2 (5 mL) at −78° C. under Ar. After stirring for an additional hour at 0° C., the reaction mixture was warmed to room temperature and treated with 1:1 CH3OH:CH2Cl2 (10 mL) with cooling and stirred 2 hr at ambient temperature. Concentration of the mixture gave oil, which was purified by flash chromatography 9:1 CH2Cl2/MeOH to give the desired product as a solid 0.13 g in 41% yield, mp: 228.4° C. 1H NMR (CD3OD) δ 8.16 (s, 1H), 7.81 (d, 2H), 7.63 (d, 2H), 6.88 (d, 2H), 6.72 (d, 2H), 3.87 (d, 1H), 3.46 (q, 4H), 1.19 (t, 6H). 13C NMR (CD3OD) δ 162.2, 158.2, 147.1, 146.7, 126.3, 126.2, 120.7, 117.7, 111.9, 110.6, 108.0, 41.1, 8.6. Anal. Calcd for C18H21N3O2.¼H2O: C, 68.43; H, 6.70; N, 13.31. Found: C, 68.36; H, 6.99; N, 13.58.

Workup

temperaturethe reaction mixture was warmed to room temperature
stirringstirred 2 hr at ambient temperature
customConcentration of the mixture gave oil, which
customwas purified by flash chromatography 9:1 CH2Cl2/MeOH

Sources & evidence

ORD record: ord-b8f3295fc73d4894a1250021ad8a0cd4
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08044241B2

Reaction notes

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