Methanol → HCID 21217941, compound

HRID 1586232Notes

Reaction equation

HRID 1586232 reaction equation
[CH2:1]([CH:3]([C:26]([OH:28])=[O:27])[N:4]([CH2:13][CH2:14][CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-])=O)=[CH:19][CH:18]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]#[N:12])[CH:6]=1)[CH3:2].CO.[H][H]>[Pd].C(OCC)(=O)C>[CH2:1]([CH:3]([C:26]([OH:28])=[O:27])[N:4]([CH2:13][CH2:14][CH2:15][CH2:16][C:17]1[CH:18]=[CH:19][C:20]([NH2:23])=[CH:21][CH:22]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]#[N:12])[CH:6]=1)[CH3:2]

Participants

6

Reactant 3

HCID 887MethanolHCID 21217997HCID 21217997, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21217941HCID 21217941, compoundYield 94.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Part D. A solution of ethyl N-[4-[4-nitrophenyl]butyl]-N-[3-cyanophenyl]glycine (0.31 gm, 0.81 mmol) and 20 mL methanol:ethyl acetate (v:v, 50:50) was degassed with nitrogen in a Parr shaker bottle, then 10% palladium on carbon was added. The reaction was charged to 50 PSI hydrogen and shaken for 1/2 hr. The catalyst was filtered off over celite, the filtrate concentrated and the product purifed by flash chropmatography on silica gel eluting ethyl acetate:methylene chloride (v:v, 10:90) to give ethyl N-[4-[4-aminophenyl]butyl]-N-[3-cyanophenyl]glycine as a semisolid 0.27 gm (94%). MS 352(M+H)+ 1 H NMR (CDCl3): 7.2(m, 1H), 7.0(m, 3H), 6.8(m, 2H), 6.6(d, 2H), 4.2(q, 2H), 4.0(s, 2H), 3.6(bs, 2H), 3.4(m, 2H), 2.6(m, 2H), 1.6(m, 4H), 1.2(t, 3H).

Workup

  1. filtrationThe catalyst was filtered off over celite
  2. concentrationthe filtrate concentrated
  3. washeluting ethyl acetate

Sources & evidence

ORD record
ord-e52a38e346974e6393637b555d9c5946
Source dataset
uspto-grants-1999_08
Patent number
US05942544

Reaction notes

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