Benzamide → 3-iodo-4-methylbenzamide
Reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5](O)=[O:6].C([NH2:20])(=O)C1C=CC=CC=1.C(Cl)(C(Cl)=O)=O.[NH4+].[OH-]>>[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([NH2:20])=[O:6]Participants
5
Procedure
3-Iodo-4-methyl benzoic acid was converted to the corresponding benzamide according to the procedure described for compound la above ((COCl)2, NH4OH), to provide 3-iodo-4-methyl benzamide in 93% yield. Further conversion according to Method B described above provided compound 10 in 48% yield. 1H NMR (CDCl3) δ 8.02 (1 H, d, J=1.6 Hz), 7.95 (1 H, d, J=7.9 Hz), 7.29 (1 H, d, J=7.9 Hz), 6.46 (1 H, d, J=15.9 Hz), 6.10 (1 H, br s), 5.75 (1 H, br s), 4.08 (2 H, q, J=7.1 Hz), 2.48 (3 H, s), 1.42 (3 H, t, J=7.1 Hz) Anal. (C13H12N2O3.0.2 H2O) C, H, N.
Sources & evidence
- ORD record
- ord-cf0986c8f7fd4d35ae9436f9f5a80dc8
- Source dataset
- uspto-grants-2002_04
- Patent number
- US06369226B1
Reaction notes
Loading…