2-(5-Methyl-7-nitro-1-indolinyl)benzoic acid → 4-Methyl-1,2-dihydrobenzo[c]pyrrolo[1,2,3-ef][1,5]benzodiazepin-7-one

HRID 4020Notes

Reaction equation

HRID 4020 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([N+:11]([O-])=O)[CH:10]=1)[N:7]([C:14]1[CH:22]=[CH:21][CH:20]=[CH:19][C:15]=1[C:16](O)=[O:17])[CH2:6][CH2:5]2>Cl.[Pd].C(O)C>[CH3:1][C:2]1[CH:10]=[C:9]2[NH:11][C:16](=[O:17])[C:15]3[CH:19]=[CH:20][CH:21]=[CH:22][C:14]=3[N:7]3[CH2:6][CH2:5][C:4]([CH:3]=1)=[C:8]23

Participants

5

Reactant 1

HCID 140236802-(5-Methyl-7-nitro-1-indolinyl)benzoic acid

Product 1

HCID 138232804-Methyl-1,2-dihydrobenzo[c]pyrrolo[1,2,3-ef][1,5]benzodiazepin-7-oneYield 66.6%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 2-(5-methyl-7-nitroindolin-1-yl)benzoic acid (9 g, 0.03 mole), conc. hydrochloric acid (several drops) and ethanol (200 ml) was added 5% palladium-charcoal (1.5 gm). The mixture was shaked under hydrogen (58 psi) for 30 hours. The solvent was removed and the residue was loaded onto a silica gel flash chromatography column (800 g, 230-400 mesh), packed and eluted with dichloromethane (4 l) and 2% methanol in dichloromethane (4 l). The fractions containing product were pooled and evaporated to yield 5 g (66%) of product. Recrystallization from chloroform gave the analytical sample, mp 222°-224° C.

Workup

  1. customThe solvent was removed
  2. washeluted with dichloromethane (4 l) and 2% methanol in dichloromethane (4 l)
  3. additionThe fractions containing product
  4. customevaporated

Sources & evidence

ORD record
ord-1a0b2efa16a04e6f9b9dd632b5d51a5a
Source dataset
uspto-grants-1988_02
Patent number
US04723007

Reaction notes

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