Acetic Acid → HCID 178469619, compound

HRID 1168524Notes

Reaction equation

HRID 1168524 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH:15]([C:17]1[CH:18]=[C:19]([CH2:33][N:34]2[CH2:39][CH2:38][O:37][CH2:36][CH2:35]2)[CH:20]=[C:21]2[C:26]=1[N:25]=[CH:24][C:23]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[C:22]2[OH:32])=O.[CH2:40]([NH2:47])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1.C(O)(=O)C>C(O)C.C1COCC1>[CH2:40]([NH:47][CH2:15][C:17]1[CH:18]=[C:19]([CH2:33][N:34]2[CH2:39][CH2:38][O:37][CH2:36][CH2:35]2)[CH:20]=[C:21]2[C:26]=1[N:25]=[CH:24][C:23]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[C:22]2[OH:32])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7504BenzylamineHCID 5049666Sodium triacetoxyborohydrideHCID 178469634HCID 178469634, compound

Product 1

HCID 178469619HCID 178469619, compoundYield 107%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

Sodium triacetoxyborohydride (1.0 g) is added to a stirred solution of ethyl 8-formyl-4-hydroxy-6-(4-morpholinylmethyl)-3-quinolinecarboxylate (Preparation 27, 515 mg), benzylamine (340 mg) and acetic acid (360 mg) in a mixture of ethanol/THF (10 mL, 1/1). The solution is stirred for 90 min. The solvents are evaporated. The residue is taken up in chloroform and is applied to a silica gel column which is eluted with 1-3% methanol/chloroform followed by 4% methanol/chloroform to afford 697 mg of the title compound which is crystallized from methanol/ether. Physical characteristics: 1H NMR (CDCl3) δ1.43, 2.47, 3.59, 3.72, 3.90, 4.26, 4.42, 7.34, 7.51, 8.23, 8.59. Anal. Found: C, 68.59; H, 6.65; N, 9.64.

Workup

  1. customThe solvents are evaporated
  2. washis eluted with 1-3% methanol/chloroform

Sources & evidence

ORD record
ord-04d9c25290284376bea8762775837e86
Source dataset
uspto-grants-2003_09
Patent number
US06624159B2

Reaction notes

Loading…