Hydrochloric Acid → HCID 9859800, compound

HRID 439848Notes

Reaction equation

HRID 439848 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]([CH3:12])[C:9]2[NH:8][C:7]3[C:13]4[C:18]([CH2:19][C:6]=3[C:5]=2[CH:4]=1)=[CH:17][CH:16]=[CH:15][CH:14]=4.O1CCN(B)CC1.Cl.O>O1CCCC1>[CH3:1][O:2][C:3]1[CH:11]=[C:10]([CH3:12])[C:9]2[NH:8][C@@H:7]3[C:13]4[C:18]([CH2:19][C@@H:6]3[C:5]=2[CH:4]=1)=[CH:17][CH:16]=[CH:15][CH:14]=4

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 962WaterHCID 5028646HCID 5028646, compoundHCID 22408513HCID 22408513, compound

Product 1

HCID 9859800HCID 9859800, compoundYield 38.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5.0 g (0.020 mol) of 5,10-dihydro-8-methoxy-6-methylindeno[1,2-b]indole in 50 ml of tetrahydrofurane was added 8.1 g (0.080 mol) of morpholino borane and dropwise 6.3 ml of conc. hydrochloric acid. The initially exothermic reaction mixture was stirred at room temperature for 72 hour. An additional 6.3 ml of conc. hydrochloric acid was then added and the mixture stirred over night. 25 ml of water was then added and the mixture evaporated. The residue was suspended in 200 ml of water and 5 ml of conc. hydrochloric acid and the mixture was heated on a water bath until most of the solid material had dissolved. The solution was then filtered hot and the filtrate cooled and alkalinized by addition of 10M sodium hydroxide solution. Filtration and washing with water gave 1.93 g (38.4%) of the title compound 1H NMR (CDCl3) δ: 2.08 (3H,s), 3.15-3.25 (1H,dd), 3,42-3.55 (1H,dd), 3.7 (3H,s), 4.1-4.22 (1H,t), 5.22-5.28 (1H,d), 6.42-6.46 (1H,d), 6.6-6.65 (1H,d), 7.14-7,25 (3H,m), 7.3-7.4 (1H,m).

Workup

  1. stirringthe mixture stirred over night
  2. customthe mixture evaporated
  3. temperature5 ml of conc. hydrochloric acid and the mixture was heated on a water bath until most of the solid material
  4. dissolutionhad dissolved
  5. filtrationThe solution was then filtered hot
  6. temperaturethe filtrate cooled
  7. additionalkalinized by addition of 10M sodium hydroxide solution
  8. filtrationFiltration
  9. washwashing with water

Sources & evidence

ORD record
ord-d718b79fe1884112801b5ab012d273cd
Source dataset
uspto-grants-1996_05
Patent number
US05516788

Reaction notes

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