Methanol → HCID 10366797, compound

HRID 1440958Notes

Reaction equation

HRID 1440958 reaction equation
[N+:1]([C:4]1[CH:30]=[C:29]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:28]=[CH:27][C:5]=1[O:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:12][C:11]=1[N+:24]([O-])=O)([O-])=O.CO.C(Cl)(Cl)Cl.C1C=C2C(C(O)(O)C(=O)C2=CC=1)=O>C(Cl)Cl.[Pt]>[NH2:24][C:11]1[CH:12]=[C:13]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:14]=[CH:15][C:10]=1[O:9][CH2:8][CH2:7][O:6][C:5]1[CH:27]=[CH:28][C:29]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[CH:30][C:4]=1[NH2:1]

Participants

7

Reactant 4

HCID 887MethanolHCID 6212ChloroformHCID 10236NinhydrinHCID 10052248HCID 10052248, compound

Product 1

HCID 10366797HCID 10366797, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 6344DichloromethaneSolvent

Procedure

Compound 9 (40 g, 77.5 mmol) is dissolved in 400 mL of CH2Cl2 and 1.5 g 5% platinum on charcoal is added. The reaction is shaken under 40 psi H2 for six hours until the reaction is judged complete using thin layer chromatography (1:9 methanol:chloroform). The product reacts with ninhydrin on a TLC plate to give a ruddy brown product with an Rf of 0.3. The reaction mixture is filtered through diatomaceous earth to remove the catalyst, and the resulting filtrate is evaporated under reduced pressure. The resulting semi-crystalline oil is stirred with 400 mL methanol for two hours while protected from light. The resulting light gray crystals are filtered and dried to give 10 in 90% yield.

Workup

  1. customto give a ruddy brown product with an Rf of 0.3
  2. filtrationThe reaction mixture is filtered through diatomaceous earth
  3. customto remove the catalyst
  4. customthe resulting filtrate is evaporated under reduced pressure
  5. stirringThe resulting semi-crystalline oil is stirred with 400 mL methanol for two hours while protected from light
  6. filtrationThe resulting light gray crystals are filtered
  7. customdried

Sources & evidence

ORD record
ord-0da0012112fd4f768a15b7994dc924af
Source dataset
uspto-grants-1996_03
Patent number
US05501980

Reaction notes

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