Hydrochloric Acid → HCID 68461355, compound

HRID 505363Notes

Reaction equation

HRID 505363 reaction equation
[CH3:1][O:2][C:3]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][C:4]=1[CH2:5][NH:6][CH2:7][CH:8](OC)OC.[CH:19](=O)[C:20]1[CH:29]=[CH:28][C:25]([O:26][CH3:27])=[C:22]([O:23][CH3:24])[CH:21]=1.[ClH:31]>>[ClH:31].[CH3:18][O:17][C:14]1[CH:15]=[CH:16][C:3]([O:2][CH3:1])=[C:4]2[C:13]=1[C:8]1[CH2:19][C:20]3[CH:29]=[CH:28][C:25]([O:26][CH3:27])=[C:22]([O:23][CH3:24])[C:21]=3[C:7]=1[N:6]=[CH:5]2

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 8419VeratraldehydeHCID 11196128HCID 11196128, compound

Product 1

HCID 68461355HCID 68461355, compoundYield 24%

Procedure

Amine 12d (2.82 g, 11.1 mmol) and veratraldehyde (10a, 4.00 g, 0.030 mol) were reacted in concentrated hydrochloric acid as described previously for compound 9aa. The product was isolated as a yellow-orange hygroscopic solid (1.01 g, 24%), mp 242-244° C. 1H NMR (300 MHz, TFA) δ 9.52 (s, 1H), 7.75 (s, 1H), 7.43 (d, J=7.8 Hz, 1H), 7.38 (s, 1H), 7.08 (d, J=8.7 Hz, 1H), 4.56 (s, 2H), 4.10 (s, 3H), 4.09 (s, 3H), 4.04 (s, 6H). Anal. (C20H20NO4Cl.1.7H2O)C, H, N, Anal. Calcd for C20H20NO4Cl(H2O)1.7: C, 59.39; H, 5.83; N, 3.46. Found: C, 59.22; H, 5.53; N, 3.72.

Sources & evidence

ORD record
ord-ef78f4a8616c44458ac6b71be15a6bef
Source dataset
uspto-grants-2010_08
Patent number
US07781445B2

Reaction notes

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