Acetaldehyde → HCID 21462916, compound

HRID 1940582Notes

Reaction equation

HRID 1940582 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]2[C:8]3[N:9]([CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=4[O:34][CH3:35])[C:10](=[O:26])[C:11]([C:23]([OH:25])=[O:24])=[C:12]([C:15]4[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=4)[C:13]=3[O:14][C:4]=2[CH:3]=1.[CH:36](=O)[CH3:37].C([BH3-])#N.[Na+].Cl>CO.[Ti](Cl)(Cl)(Cl)Cl>[CH2:36]([NH:1][C:2]1[CH:7]=[CH:6][C:5]2[C:8]3[N:9]([CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=4[O:34][CH3:35])[C:10](=[O:26])[C:11]([C:23]([OH:25])=[O:24])=[C:12]([C:15]4[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=4)[C:13]=3[O:14][C:4]=2[CH:3]=1)[CH3:37]

Participants

7

Reactant 4

HCID 177AcetaldehydeHCID 313Hydrochloric AcidHCID 5003444Sodium cyanoborohydrideHCID 21462925HCID 21462925, compound

Product 1

HCID 21462916HCID 21462916, compound

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 887MethanolSolvent

Procedure

A solution of 6 g of 7-amino-1,2-dihydro-1-(2-methoxybenzyl)-4-(4-methoxyphenyl)-2-oxobenzofuro-[3,2-b]pyridine-3-carboxylic acid and 0.5 g of titanium tetrachloride in 100 ml of methanol is treated with 1 ml of freshly distilled acetaldehyde. 4 g of sodium cyanoborohydride are then added and the mixture is stirred for 30 hours. Half-concentrated hydrochloric acid is added, the mixture is worked up in the customary manner and 7-ethylamino-1,2-dihydro-1-(2-methoxybenzyl)-4-(4-methoxyphenyl)-2-oxobenzofuro-[3,2-b]pyridine-3-carboxylic acid is obtained.

Sources & evidence

ORD record
ord-a5a309c6faa1480e87e1ab6a154410de
Source dataset
uspto-grants-1997_12
Patent number
US05700807

Reaction notes

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