Methanol → HCID 14478923, compound

HRID 620007Notes

Reaction equation

HRID 620007 reaction equation
[NH2:1][C:2]1[N:11]=[C:10]([NH2:12])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH:14]=[CH:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[C:8]=2[CH3:13])[N:3]=1.CO>[Pt]=O.CCO>[NH2:1][C:2]1[N:11]=[C:10]([NH2:12])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[C:8]=2[CH3:13])[N:3]=1

Participants

5

Reactant 2

HCID 887MethanolHCID 54041024HCID 54041024, compound

Product 1

HCID 14478923HCID 14478923, compound

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

A mixture of 12.6 g of the olefin mixture of Example 5, 2.0 g of platinum oxide, and 500 ml of methanol was stirred under an atmosphere of hydrogen for 60 h. The catalyst was removed by filtration through a celite pad and the filtrate was evaporated in vacuo. The solid residue was recrystallized from ethanol to afford 10.6 g (83%), m.p. 262°-264° C.; UV (95% EtOH; pH 12). 238 (43,600), 272 (10,900), 347 (5,930); NMR (CDCl3 --CD3OD) 0.89 (3H, t, CH3CH2 --), 1.32 (12H, m, CH2), 2.72 (3H, s, 5--CH3), 2.72 (2H, t, Ar--CH2), 7.20 (1H, d, C7 --H), 7.47 (1H, d, C8 --H). Anal. calc'd for C17H26N4.HCl: C, 63.2; H, 8.43; N, 17.3; Cl, 11.0. Found: C, 63.3; H, 8.46; N, 17.3; Cl, 10.9.

Workup

  1. customThe catalyst was removed by filtration through a celite pad
  2. customthe filtrate was evaporated in vacuo
  3. customThe solid residue was recrystallized from ethanol
  4. customto afford 10.6 g (83%), m.p. 262°-264° C.

Sources & evidence

ORD record
ord-d5a6744253bf424c883c396771a53846
Source dataset
uspto-grants-1989_04
Patent number
US04818753

Reaction notes

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