4-Methylbenzaldehyde → HCID 178423711, compound

HRID 1059068Notes

Reaction equation

[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH2:16][C:17]2[N:22]=[C:21]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[N:20]=[C:19]([OH:29])[CH:18]=2)=[CH:6][CH:5]=1)(C)C.CC1C=CC(C=O)=CC=1>>[CH3:1][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH2:16][C:17]2[N:22]=[C:21]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[N:20]=[C:19]([OH:29])[CH:18]=2)=[CH:8][CH:9]=1

Participants

Reactant 2

HCID 77254-Methylbenzaldehyde

HCID 178438860HCID 178438860, compound

Product 1

HCID 178423711HCID 178423711, compound

Procedure

Compound 7 was prepared using the synthetic route for Compound 6 using 4-methylbenzaldehyde in procedure 5. Purification was accomplished using column chromatography to provide the title compound as a solid (mp 210-214° C.). 1H-NMR (CDCl3) δ 8.1 (m, 2H); 7.5 (m, 3H); 7.3-7.2 (m, 5H); 7.1 (s, 4H); 6.2(s, 1H), 5.4 (s, 1H); 2.3 (s,3H). 13C-NMR (CDCl3) δ 170.9; 165.6; 156.5; 141.4; 138.2; 136.6; 132.1; 132.0; 129.4; 129.32; 129.29; 129.0; 128.5; 127.9; 126.9; 112.5; 58.4; 20.9. Mass spec (MH+ 353). Analysis for C24H20N2O; calculated, C 81.79, H 5.72, N 7.95; found C 81.43, H 5.91, N 7.75.

Workup

customCompound 7 was prepared
customPurification

Sources & evidence

ORD record: ord-da61f51317064047b566c0aad87b6992
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06518424B1

Reaction notes

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