Ethanol → HCID 66699704, compound

HRID 388125Notes

Reaction equation

HRID 388125 reaction equation
[C:1]1([C@H:7]([NH:9][C:10]2[C:15]([NH2:16])=[CH:14][CH:13]=[C:12]([C:17]3[CH:26]=[CH:25][CH:24]=[C:23]4[C:18]=3[CH:19]=[CH:20][CH:21]=[N:22]4)[N:11]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N+](C1C(N[C@@H](C2C=CC=CC=2)C)=NC(C2C=CC=C3C=2C=CC=N3)=CC=1)([O-])=O.[CH2:55]([OH:57])C>[Pd]>[C:1]1([C@H:7]([N:9]2[C:10]3=[N:11][C:12]([C:17]4[CH:26]=[CH:25][CH:24]=[C:23]5[C:18]=4[CH:19]=[CH:20][CH:21]=[N:22]5)=[CH:13][CH:14]=[C:15]3[NH:16][C:55]2=[O:57])[CH3:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 66699880HCID 66699880, compoundHCID 68853627HCID 68853627, compound

Product 1

HCID 66699704HCID 66699704, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

(R)—N2-(1-Phenylethyl)-6-(quinolin-5-yl)pyridine-2,3-diamine. A solution of (R)-3-nitro-N-(1-phenylethyl)-6-(quinolin-5-yl)pyridin-2-amine (1.10 g, 2.97 mmol) in ethanol (95 mL) was purged with nitrogen for several minutes. Following addition of palladium on carbon (0.125 g, 1.18 mmol), the flask was evacuated and a hydrogen filled balloon was placed on the reaction. After stirring at room temperature for 18 h, the reaction was filtered and the solvent removed under reduced pressure to afford the title compound (0.77 g, 76% yield). MS (ESI) m/z 341.3 [M+1]+.

Workup

  1. customthe flask was evacuated
  2. customa hydrogen filled balloon was placed on the reaction
  3. filtrationthe reaction was filtered
  4. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-c78f2e2088dd4304ac1db6a6e8129a82
Source dataset
uspto-grants-2013_02
Patent number
US08372976B2

Reaction notes

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