Ammonium Hydroxide → HCID 12519150, compound

HRID 2052709Notes

Reaction equation

HRID 2052709 reaction equation
[CH2:1]1[N:9]2[C:10]3[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=3[N:12]=[CH:13][C:7]3=[C:8]2[C:3](=[CH:4][CH:5]=[CH:6]3)[CH2:2]1.[CH3:18][Mg]Br.[NH4+].[OH-]>O1CCCC1.CCOCC>[CH3:18][CH:13]1[NH:12][C:11]2[CH:14]=[CH:15][CH:16]=[CH:17][C:10]=2[N:9]2[CH2:1][CH2:2][C:3]3=[CH:4][CH:5]=[CH:6][C:7]1=[C:8]23

Participants

6

Reactant 3

HCID 14923Ammonium HydroxideHCID 125191331,2-Dihydroindolo[1,7-ab][1,5]benzodiazepineHCID 178418573HCID 178418573, compound

Product 1

HCID 12519150HCID 12519150, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2.00 g of 1,2-dihydroindolo[1,7-ab][1,5]benzodiazepine in 40 ml of tetrahydrofuran, cooled under N2 to 0° C., is added dropwise 10 ml of a 2.5 molar solution of methyl magnesium bromide in ether. The reaction mixture is refluxed for 3 hours, cooled, and treated cautiously with saturated aqueous NH4OH solution. The mixture is partitioned between CH2Cl2 and water. The organic phase is separated, washed once with brine, dried over Na2SO4 and concentrated to a solid of 6-methyl-1,2,6,7-tetrahydroindolo[1,7-ab][1,5]benzodiazepine, m.p. 134°-136° C.

Workup

  1. temperatureThe reaction mixture is refluxed for 3 hours
  2. temperaturecooled
  3. customThe mixture is partitioned between CH2Cl2 and water
  4. customThe organic phase is separated
  5. washwashed once with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated to a solid of 6-methyl-1,2,6,7-tetrahydroindolo[1,7-ab][1,5]benzodiazepine, m.p. 134°-136° C.

Sources & evidence

ORD record
ord-cdf2fc97e4c44fb4951d954e6bf77cc4
Source dataset
uspto-grants-1980_01
Patent number
US04186199

Reaction notes

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