Acetyl chloride → 1,5-Dihydro-3-methyl-[1,2]diazepino[4,5,6-cd]-indol-6-one

HRID 2298910Notes

Reaction equation

HRID 2298910 reaction equation
[C:1]1([C:7]2[C:13]3=[CH:14][NH:15][C:16]4[CH:17]=[CH:18][CH:19]=[C:11]([C:12]=43)[C:10](=[O:20])[NH:9][N:8]=2)C=CC=CC=1.N1C2C=CC=C(C(OC)=O)C=2C=C1.C(Cl)(=O)C.[Cl-].[Al+3].[Cl-].[Cl-].O.NN>ClC(Cl)C.CO.Cl>[CH3:1][C:7]1[C:13]2=[CH:14][NH:15][C:16]3[CH:17]=[CH:18][CH:19]=[C:11]([C:12]=32)[C:10](=[O:20])[NH:9][N:8]=1

Participants

9

Reactant 5

HCID 6367Acetyl chlorideHCID 24654Hydrazine hydrate (1:1)HCID 2733668methyl 1H-indole-4-carboxylateHCID 6451240Aluminum(III) ChlorideHCID 1354630341,5-Dihydro-3-phenyl-[1,2]diazepino[4,5,6-cd]-indol-6-one

Product 1

HCID 1355841831,5-Dihydro-3-methyl-[1,2]diazepino[4,5,6-cd]-indol-6-one

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 63651,1-DichloroethaneSolvent

Procedure

In a manner similar to that described for compound 28, a solution of methyl indole-4-carboxylate (427 mg, 2.44 mmol) in dichloroethane (7 mL) was treated with acetyl chloride (0.5 mL) and aluminum chloride (130 mg). The intermediate ketone (198 mg, 0.92 mmol) in MeOH (5 mL) and conc. HCl (0.05 mL) was treated, as described, with hydrazine hydrate (0.1 mL). The product precipitated, was collected by filtration and rinsed with ice-cold MeOH to give 1,5-dihydro-3-methyl-[1,2]diazepino[4,5,6-cd]-indol-6-one, 168 mg (92%) as a bright yellow solid: m.p. 335-336° C.; 1H NMR (300 MHz, d6-DMSO) δ2.17 (s, 3H), 7.19 (t, J=7.8 Hz, 1H), 7.54 (m, 2H), 7.67 (d, J=2.8 Hz, 1H), 10.12 (s, 1H), 11.90 (br s, 1H). HRMS (FAB, MH+) Calcd for C11H10N3O: 200.0824. Found: 200.0827. Anal. (C11H9N3O) C, H, N.

Workup

  1. customThe product precipitated
  2. filtrationwas collected by filtration
  3. washrinsed with ice-cold MeOH

Sources & evidence

ORD record
ord-57b9b74fec7b4060873d82ca283e01bf
Source dataset
uspto-grants-2002_12
Patent number
US06495541B1

Reaction notes

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