Acetic Acid → HCID 70278872, compound

HRID 365537Notes

Reaction equation

HRID 365537 reaction equation
[CH2:1]([O:3][C:4](=[O:28])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[CH:21]=[C:20]3[C:15]([C:16]([CH3:26])([CH3:25])[CH2:17][CH2:18][N:19]3[CH:22]([CH3:24])[CH3:23])=[CH:14][C:13]=2[CH3:27])=[CH:7][CH:6]=1)[CH3:2].[CH:29](=O)[CH3:30].C([BH3-])#N.[Na+].[C:36](O)(=O)[CH3:37]>C(#N)C>[CH2:1]([O:3][C:4](=[O:28])[C:5]1[CH:6]=[CH:7][C:8]([N:11]([C:12]2[CH:21]=[C:20]3[C:15]([C:16]([CH3:25])([CH3:26])[CH2:17][CH2:18][N:19]3[CH:22]([CH3:23])[CH3:24])=[CH:14][C:13]=2[CH3:27])[CH2:36][CH2:37][CH2:29][CH3:30])=[CH:9][CH:10]=1)[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 177AcetaldehydeHCID 5003444Sodium cyanoborohydrideHCID 9951833HCID 9951833, compound2×

Product 1

HCID 70278872HCID 70278872, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 4-(1-isopropyl-4,4,6-trimethyl-1,2,3,4-tetrahydroquinolin-7-ylamino)-benzoic acid ethyl ester (Compound 46, 64.4 mg, 0.1692 mmol), acetaldehyde (37.2 mg, 0.8462 mmol), sodium cyanoborohydride (53.2 mg, 0.8462 mmol), acetic acid (0.125 mL), and acetonitrile (1 mL) was stirred at room temperature overnight. The solvent was removed and the residue was purified by silica gel chromatography (10% ethyl acetate in hexane, Rf=0.44) to give the title compound (71.2 mg, 52%) as a solid: 1H NMR (300 MHz, CDCl3): δ1.15 (d, 6 H, J=6.5 Hz), 1.27 (t, 3 H, J=7.1 Hz), 1.31 (s, 6 H), 1.35 (t, 3 H, J=7.1 Hz), 1.74 (t, 2 H, J=6.0 Hz), 1.96 (s, 3 H), 3.15 (t, 2 H, J=6.0 Hz), 3.68 (d, 2 H, J=5.9), 3.98 (sp, 1 H, J=6.5 Hz), 4.31 (q, 2 H, J=7.1 Hz), 6.43 (s, 1 H), 6.49 (d, 2 H, J=8.9 Hz), 7.08 (s, 1 H), 7.84 (d, 2 H, J=8.9 Hz).

Workup

  1. customThe solvent was removed
  2. customthe residue was purified by silica gel chromatography (10% ethyl acetate in hexane, Rf=0.44)

Sources & evidence

ORD record
ord-46a81c1f878e445383ad0cb9cb4f9925
Source dataset
uspto-grants-2000_10
Patent number
US06127382

Reaction notes

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