Sodium Hydroxide → HCID 1229702, compound

HRID 439844Notes

Reaction equation

HRID 439844 reaction equation
[CH:1]([C:4]1[CH:12]=[CH:11][C:10]2[NH:9][C:8]3[C:13]4[C:18]([CH2:19][C:7]=3[C:6]=2[CH:5]=1)=[CH:17][CH:16]=[CH:15][CH:14]=4)([CH3:3])[CH3:2].C([BH3-])#N.[Na+].[OH-].[Na+]>C(O)(=O)C>[CH:1]([C:4]1[CH:12]=[CH:11][C:10]2[NH:9][C@@H:8]3[C:13]4[C:18]([CH2:19][C@@H:7]3[C:6]=2[CH:5]=1)=[CH:17][CH:16]=[CH:15][CH:14]=4)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 19780370HCID 19780370, compound

Product 1

HCID 1229702HCID 1229702, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

5,10-Dihydro-8-iso-propylindeno [1,2-b]indole (5.27 g, 21.3 mmol) was stirred at room temperature in glacial acetic acid (100 cm3). Sodium cyanoborohydride (5 g, 3 equivalents) was added portionwise over a period of 30 minutes. The reaction was stirred for a further 30 minutes, and then poured into ice/water (150 cm3). After stirring for 30 minutes, the solution was neutralised with aqueous 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 give the title compound as a colourless solid. Yield: 3.25 g (61%). M.p. 104° C. [from petrol (60°-80° C.)]. 1H NMR (CDCl3) δ: 1.19 (6H, d,), 2.80 (1H, septet,), 3.20 (1H, dd,), 3.48 (1H, dd,), 4.07 (1H, br,), 4.15 (1H, ddd,), 5.21 (1H, d,), 6.53 (1H, d,), 6.86 (1H, dd,), 7.03 (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-373ed67b0bf649f1902d39508f6af881
Source dataset
uspto-grants-1996_05
Patent number
US05516788

Reaction notes

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