HCID 59807107, compound → HCID 59807136, compound

HRID 1922408Notes

Reaction equation

HRID 1922408 reaction equation
[CH3:1][N:2]([CH3:20])[CH2:3][CH2:4][N:5]1[C:11](=[O:12])[CH2:10][CH2:9][CH2:8][C:7]2[CH:13]=[CH:14][CH:15]=[C:16]([N+:17]([O-])=O)[C:6]1=2>C(O)C.C1COCC1.[Pd]>[NH2:17][C:16]1[C:6]2[N:5]([CH2:4][CH2:3][N:2]([CH3:20])[CH3:1])[C:11](=[O:12])[CH2:10][CH2:9][CH2:8][C:7]=2[CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 1

HCID 59807107HCID 59807107, compound

Product 1

HCID 59807136HCID 59807136, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

1-(2-(dimethylamino)ethyl)-9-nitro-4,5-dihydro-1H-benzo[b]azepin-2(3H)-one (100 mg, 0.361 mmol) was stirred to dissolve in a mixture of ethanol (4 mL) and THF (3 mL). To this solution was added palladium on carbon, 10 wt %, (40 mg) as a solid. The black suspension was stirred under hydrogen gas for 3 h. When TLC analysis showed that the starting material was consumed the reaction mixture was filtered through a pad of celite and washed with methanol. The filtrate was concentrated and then chromatographed on silica gel in 10% 2 N NH3/MeOH in dichloromethane. Yield 90 mg (quantitative). 1H NMR (DMSO-d6) δ 6.86 (d, 1H, J=8.1 Hz), 6.53 (d, 1H, J=3.0 Hz), 6.38 (dd, 1H, J=8.1, 3.0 Hz), 5.02 (brs, 2H), 2.50 (m, 2H), 2.25 (m, 2H), 1.8-2.2 (m, 10H); ESI-MS (m/z, %): 248 (MH+, 58), 203 (100).

Workup

  1. customwas consumed the reaction mixture
  2. filtrationwas filtered through a pad of celite
  3. washwashed with methanol
  4. concentrationThe filtrate was concentrated
  5. customchromatographed on silica gel in 10% 2 N NH3/MeOH in dichloromethane

Sources & evidence

ORD record
ord-a388dedec90346d99360f2e48ccbe9f4
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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