Dimethylamine → HCID 86746312, compound

HRID 373201Notes

Reaction equation

C1C=[CH:5][NH+:4]=[CH:3]C=1.Br[Br-]Br.[CH2:10]([O:12][C:13]([C:15]1[CH:20]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[CH:27]=[O:28])[C:19]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[C:18](C)[NH:17][C:16]=1[CH3:35])=[O:14])[CH3:11].N1C=CC=C[CH:37]=1.CNC>ClCCl>[CH2:32]([O:31][C:29]([C:19]1[CH:20]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[CH:27]=[O:28])[C:15]([C:13]([O:12][CH2:10][CH3:11])=[O:14])=[C:16]([CH3:35])[N:17]([CH3:37])[C:18]=1[N:4]([CH3:5])[CH3:3])=[O:30])[CH3:33]

Participants

Conditions

Temperature: -10 °C

Procedure

Pyridine hydrobromide perbromide (3.2 g) was added to a solution of 4-(2-formylphenyl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylic acid diethylester (3.15 g) and pyridine (1.3 ml) in dicloromethane (100 ml) at 0° C. and stirred for 0.5 hours. The mixture was then cooled to -10° C., treated with dimethylamine (10.6 ml) and stirred at -10° C. for 1 hour. The solvent was evaporated and the residue taken up with ethyl acetate. The solid was filtered off and the solution evaporated to dryness to obtain a red oil, which was eluted on a silica gel column (Ethyl acetate/Petrol ether/Methanol, 7:3:1) to yield the title compound as a yellow solid (from petrol ether) (2.3 g), m.p. 115°-120° C. T.l.c. (CH2Cl2 /Methanol, 95:5) Rf. 0.38.

Workup

stirringstirred at -10° C. for 1 hour
customThe solvent was evaporated
filtrationThe solid was filtered off
customthe solution evaporated to dryness
customto obtain a red oil, which
washwas eluted on a silica gel column (Ethyl acetate/Petrol ether/Methanol, 7:3:1)

Sources & evidence

ORD record: ord-f8c0924b1447449298cf31a8d62cfab5
Source dataset: uspto-grants-1992_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05162345

Reaction notes

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