Methanol → HCID 21071398, compound

HRID 1371919Notes

Reaction equation

HRID 1371919 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[CH2:13][CH2:14][N:15]1[C:23](=[O:24])[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]1=[O:25])([O-])=O.CO>O=[Pt]=O.C1COCC1>[NH2:1][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[CH2:13][CH2:14][N:15]1[C:16](=[O:25])[C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:23]1=[O:24]

Participants

5

Reactant 2

HCID 887MethanolHCID 227222762-[2-(5-Nitro-1H-indol-3-yl)ethyl]-1H-isoindole-1,3(2H)-dione

Product 1

HCID 21071398HCID 21071398, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Combine a mixture of 2-(2-(5-nitro-1H-indol-3-yl)ethyl)isoindole-1,3-dione (1.8 g, 5.4 mmol), PtO2 (500 mg), 100 mL MeOH and 100 mL THF and hydrogenate at atmospheric pressure overnight. Filter the reaction through a pad of celite and concentrate to dryness. Redissolve the residue in 50/50 chloroform/dichloromethane and refilter through a pad of celite. Concentration under vacuum give the title compound as a dark solid: ISMS 306 (M+1); Analysis for C18H13N3O4 0.1C7H8 0.2 dichloromethane: calcd: C, 68.70; H, 4.89; N, 12.58; found: C, 69.08; H, 4.75; N, 12.69; 1H NMR (CDCl3) 7.9–7.8 (m, 3H), 7.75–7.65 (m, 2H), 7.2–7.1 (m, 1H), 7.05–7.0 (m, 2H), 6.7–6.6 (m, 1H), 4.0–3.9 (m, 2H), 3.4 (bs, 2H), 3.1–3.0 (m, 2H).

Workup

  1. customhydrogenate at atmospheric pressure overnight
  2. filtrationFilter
  3. customthe reaction through a pad of celite
  4. concentrationconcentrate to dryness
  5. dissolutionRedissolve the residue in 50/50 chloroform/dichloromethane and refilter through a pad of celite
  6. concentrationConcentration under vacuum

Sources & evidence

ORD record
ord-e30219c9945143ddb14676365a6ecbe3
Source dataset
uspto-grants-2007_01
Patent number
US07157488B2

Reaction notes

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