4-Nitrobenzaldehyde → HCID 67185728, compound

HRID 735929Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Cl:10])[CH:9]=1)[CH2:5][NH2:6].[N+:11]([C:14]1[CH:21]=[CH:20][C:17]([CH:18]=O)=[CH:16][CH:15]=1)([O-:13])=[O:12]>>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Cl:10])[CH:9]=1)[CH2:5][NH:6][CH2:18][C:17]1[CH:20]=[CH:21][C:14]([N+:11]([O-:13])=[O:12])=[CH:15][CH:16]=1

Participants

Reactant 2

HCID 5414-Nitrobenzaldehyde

HCID 457602Benzenemethanamine, 3,5-dichloro-

Product 1

HCID 67185728HCID 67185728, compoundYield 71%

Procedure

The same procedure as employed in the preparation of Example 226 (step a) but using 3,5-dichlorobenzylamine and 4-nitrobenzaldehyde gave the title compound as a yellow powder (71%). 1H NMR (CD3OD, 300 MHz) δ 8.37 (d, 2H, J=8.8 Hz), 7.83 (d, 2H, J=8.8 Hz), 7.61 (br s, 3H), 4.48 (s, 2H), 4.38 (s, 2H). M−(LC/MS(ESI)): 309; M+(LC/MS(ESI)): 311 HPLC (Condition A), Rt: 2.78 min (HPLC purity: 93.0%).

Workup

customThe same procedure as employed in the preparation of Example 226 (step a) but

Sources & evidence

ORD record: ord-26ab6c17e6e844639a9a3f1bb56ebe28
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07592477B2

Reaction notes

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