Sodium Hydroxide → HCID 57079581, compound

HRID 439843Notes

Reaction equation

HRID 439843 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:8]2[NH:7][C:6]3[C:11]4[C:16]([CH2:17][C:5]=3[C:4]=2[CH:3]=1)=[CH:15][CH:14]=[CH:13][CH:12]=4.C([BH3-])#N.[Na+].[OH-].[Na+]>C(O)(=O)C>[CH3:1][C:2]1[CH:10]=[CH:9][C:8]2[NH:7][C@@H:6]3[C:11]4[C:16]([CH2:17][C@@H:5]3[C:4]=2[CH:3]=1)=[CH:15][CH:14]=[CH:13][CH:12]=4

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 222470798-Methyl-5,10-dihydroindeno[1,2-b]indole

Product 1

HCID 57079581HCID 57079581, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

5,10-Dihydro-8-methylindeno[1,2-b]indole (10 g, 46 mmol) was stirred at room temperature in glacial acetic acid (150 cm3). Sodium cyanoborohydride (8.6 g, 3 equivalents) was added portionwise over a period of 30 minutes. The reaction was stirred for a further hour, and then poured into ice/water (200 cm3). After stirring for 30 minutes, the acidic solution was made basic by the addition of sodium hydroxide, and the colourless solid thus formed collected by filtration. This solid was washed copiously with water until the residue was free from cyanide ion, and then dried in a vacuum oven to yield the title compound as a colourless solid. Yield: 7.5 g (73%) M.p. 110° C. (from ethanol/water). 1H NMR (CDCl3) δ: 2.24 (3H, s,), 3.20 (1H, dd,), 3.50 (1H, dd,) 3.9 (1H, br,), 4.16 (1H, dd,), 5.23 (1H, d,), 6.52 (1H,d,), 6.80 (1H, d,), 6.99 (1H, s,), 7.1-7.4 (4H, m,).

Workup

  1. stirringAfter stirring for 30 minutes
  2. customthe colourless solid thus formed
  3. filtrationcollected by filtration
  4. washThis solid was washed copiously with water until the residue
  5. customdried in a vacuum oven

Sources & evidence

ORD record
ord-ca0f4c6f72a8490da954a345f5cf53e7
Source dataset
uspto-grants-1996_05
Patent number
US05516788

Reaction notes

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