Dimethylamine, hydrochloride → HCID 178513705, compound

HRID 234286Notes

Reaction equation

HRID 234286 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]([C:12](Cl)=[O:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.Cl.C[NH:17]C.[CH:19]([N:22]([CH:25]([CH3:27])C)CC)([CH3:21])C.C(=O)(O)[O-].[Na+]>ClCCl>[N:22]1([C:11]2[C:2]([OH:1])=[N:3][C:4]3[C:9]([C:10]=2[C:12]([NH2:17])=[O:13])=[CH:8][CH:7]=[CH:6][CH:5]=3)[CH2:19][CH2:21][CH2:27][CH2:25]1

Participants

6

Reactant 4

HCID 10473Dimethylamine, hydrochlorideHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 178521120HCID 178521120, compound

Product 1

HCID 178513705HCID 178513705, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 2-hydroxyquinolin-4-oyl chloride (V-A, 0.90 g) in dichloromethane (20 ml) are added dimethylamine hydrochloride (0.52 g), followed by diisopropylethylamine (1.12 ml). After stirring for 5 hr aqueous sodium bicarbonate is added and the mixture is extracted several times with dichloromethane. The organic layers are dried over sodium sulfate and concentrated. The crude product was chromatographed (silica gel; methanol/dichloromethane (2/98 to 4/96)), to give dimethylamino 2-hydroxyquinoline-4-carboxamide (VI, 0.73 g), mp 219°-220°.

Workup

  1. additionis added
  2. extractionthe mixture is extracted several times with dichloromethane
  3. dry with materialThe organic layers are dried over sodium sulfate
  4. concentrationconcentrated
  5. customThe crude product was chromatographed (silica gel; methanol/dichloromethane (2/98 to 4/96))

Sources & evidence

ORD record
ord-a1116181b1244613ab790a310a4eb4fe
Source dataset
uspto-grants-1997_01
Patent number
US05594140

Reaction notes

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