Ethanol → HCID 66699704, compound

HRID 1014721Notes

Reaction equation

HRID 1014721 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-e2a79990628a4d56aa9d9133cab8451d
Source dataset
uspto-grants-2011_07
Patent number
US07981893B2

Reaction notes

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