Water → HCID 44549536, compound

HRID 2238417Notes

Reaction equation

HRID 2238417 reaction equation
[Cl:1][CH2:2][CH:3]1[C:11]2[C:10]3[CH:12]=[C:13]([C:16]([O:18][CH3:19])=[O:17])[CH:14]=[CH:15][C:9]=3[C:8]([N+:20]([O-:22])=[O:21])=[CH:7][C:6]=2[N:5](C(=O)C(F)(F)F)[CH2:4]1.C([O-])([O-])=O.[Cs+].[Cs+].O>CO.C(Cl)Cl>[Cl:1][CH2:2][CH:3]1[C:11]2[C:10]3[CH:12]=[C:13]([C:16]([O:18][CH3:19])=[O:17])[CH:14]=[CH:15][C:9]=3[C:8]([N+:20]([O-:22])=[O:21])=[CH:7][C:6]=2[NH:5][CH2:4]1

Participants

6

Reactant 3

HCID 962WaterHCID 10796Cesium carbonateHCID 44549272HCID 44549272, compound

Product 1

HCID 44549536HCID 44549536, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 184 (100 mg, 0.24 mmol) and Cs2CO3 (312 mg, 0.96 mmol) in MeOH (10 mL) and CH2Cl2 (15 mL) was stirred for 1.5 h. Water was added and the mixture was extracted with CH2Cl2 (×3). The combined organic extracts were washed with water, brine and dried. The solvent was evaporated and the residue was dissolved in CH2Cl2MeOH and, solvents were evaporated under reduced pressure until precipitation began. The precipitate was filtered off and washed with MeOH to give methyl 1-(chloromethyl)-5-nitro-1,2-dihydro-3H-benzo[e]indole-8-carboxylate (186) (76 mg, 100%): mp 161-163° C.; 1H NMR [(CD3)2SO] δ 8.40 (dd, J=1.6, 0.6 Hz, 1H), 8.22 (dd, J=9.1, 0.4 Hz, 1H), 7.82 (dd, J=9.1, 1.7 Hz, 1H), 7.78 (s, 1H), 6.49 (d, J=1.6 Hz, 1H), 4.35-4.28 (m, 1H), 3.93 (s, 3H), 3.89-3.82 (m, 2H), 3.79-3.69 (m, 2H). HRMS (CI) calcd. for C15H1335ClN2O4 (M+) m/z 320.0534, found 320.0563.

Workup

  1. extractionthe mixture was extracted with CH2Cl2 (×3)
  2. washThe combined organic extracts were washed with water, brine
  3. customdried
  4. customThe solvent was evaporated
  5. dissolutionthe residue was dissolved in CH2Cl2MeOH and, solvents
  6. customwere evaporated under reduced pressure until precipitation
  7. filtrationThe precipitate was filtered off
  8. washwashed with MeOH

Sources & evidence

ORD record
ord-3e6034e77cd246be8cc13784451741ef
Source dataset
uspto-grants-2010_05
Patent number
US07718688B2

Reaction notes

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