1,3-Dihydro-1,3-dioxo-2H-isoindole-2-butanal → HCID 69178387, compound

HRID 899673Notes

Reaction equation

HRID 899673 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[CH2:8][CH2:7][CH2:6][CH:5]([NH2:12])[C:4]=2[N:3]=1.[O:13]=[C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16](=[O:23])[N:15]1[CH2:24][CH2:25][CH2:26][CH:27]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[CH2:8][CH2:7][CH2:6][CH:5]([NH:12][CH2:27][CH2:26][CH2:25][CH2:24][N:15]3[C:16](=[O:23])[C:17]4[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=4)[C:14]3=[O:13])[C:4]=2[N:3]=1

Participants

6

Reactant 4

HCID 771501,3-Dihydro-1,3-dioxo-2H-isoindole-2-butanalHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 98555602-methyl-5,6,7,8-tetrahydroquinolin-8-ylamine

Product 1

HCID 69178387HCID 69178387, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-methyl-5,6,7,8-tetrahydroquinolin-8-ylamine (237 mg, 1.46 mmol) in CH2Cl2 (20 mL) at room temperature under inert atmosphere was added 4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-butyraldehyde (159 mg, 0.731 mmol) followed by sodium triacetoxyborohydride (309 mg, 2.92 mmol). The reaction mixture was stirred at room temperature for 2 hours. Saturated sodium bicarbonate solution (10 mL) was added and the mixture was extracted with dichloromethane (3×20 mL). The combined organic extracts were washed with brine, dried (MgSO4), filtered and concentrated. The resultant material was purified by column chromatography on silica gel (10:1:0.5 CH2Cl2: MeOH: NH4OH) to provide the product as a yellow oil (210 mg, 79%): 1H NMR (CDCl3): δ 1.56-1.83 (m, 6H), 1.90-2.04 (m, 2H), 2.04-2.18 (m, 2H), 2.47 (s, 3H), 2.64-2.80 (m, 4H), 3.70-3.76 (m, 3H), 6.90 (d, 1H, J=7.8 Hz), 7.24 (d, 1H, J=7.8 Hz), 7.69-7.73 (m, 2H), 7.81-7.85 (m, 2H).

Workup

  1. extractionthe mixture was extracted with dichloromethane (3×20 mL)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resultant material was purified by column chromatography on silica gel (10:1:0.5 CH2Cl2: MeOH: NH4OH)

Sources & evidence

ORD record
ord-3c9c1c59aee94f50812f0f34313e0cc0
Source dataset
uspto-grants-2008_04
Patent number
US07354932B2

Reaction notes

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