Sodium Hydroxide → HCID 57223134, compound

HRID 439846Notes

Reaction equation

HRID 439846 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH3:20])=[C:5]2[C:16](=[CH:17][C:18]=1[CH3:19])[C:8]1[NH:9][C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=3[C:7]=1[CH2:6]2.C([BH3-])#N.[Na+].[OH-].[Na+]>C(O)(=O)C>[CH3:1][O:2][C:3]1[C:4]([CH3:20])=[C:5]2[C:16](=[CH:17][C:18]=1[CH3:19])[C@H:8]1[NH:9][C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=3[C@H:7]1[CH2:6]2

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 14032101HCID 14032101, compound

Product 1

HCID 57223134HCID 57223134, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

5,10-Dihydro-2-methoxy-1,3-dimethylindeno[1,2-b]indole (1 g, 3.80 mmol) was stirred at room temperature in glacial acetic acid (15 cm3). Sodium cyanoborohydride (0.75 g, 3 equivalents) was added portionwise over 15 minutes, and the reaction stirred for a further two hours. The reaction was poured into ice/water (30 cm3), and stirred for a further 30 minutes. The solution was neutralised with aqueous sodium hydroxide, and extracted into diethyl ether. The organic extracts were copiously washed with water until the washings were free of cyanide ion. The solvent was removed in vacuo to give the title compound. This was purified by column chromatography to a colourless solid. Yield: 0.8 g (79%). M.p. 117° C. from EtOAc/petrol (60°-80° C.). Elementary analysis: Found: C 81.6, H 7.3, N 5.8, C18H19NO Calc. for C 81.5, H 7.2, N 5.9, 1H NMR (CDCl3) δ: 2.15 (3H, s,), 2.25 (3H, s,), 3.07 (1H, dd,), 3.36 (1H, dd,), 3.64 (3H, s,), 4.1 (1H, br,), 4.19 (1H, ddd,), 5.20 (1H, d,), 6.60 (1H, d,), 6.74 (1H, ddd,), 6.97 (1H, s,), 7.00 (1H, ddd,), 7.17 (1H, d,).

Workup

  1. stirringstirred for a further 30 minutes
  2. extractionextracted into diethyl ether
  3. washThe organic extracts were copiously washed with water until the washings
  4. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-7184d12b2b2148c2b21a7f2f102afecf
Source dataset
uspto-grants-1996_05
Patent number
US05516788

Reaction notes

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