Sodium Hydroxide → HCID 15082726, compound

HRID 439836Notes

Reaction equation

HRID 439836 reaction equation
[CH:1]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:2]=1[CH2:3][C:4]1[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[NH:6][C:5]=12.C([BH3-])#N.[Na+].[OH-].[Na+]>C(O)(=O)C>[CH:1]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:2]=1[CH2:3][C@@H:4]1[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[NH:6][C@@H:5]12

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 975985,10-Dihydroindeno[1,2-b]indoleHCID 5003444Sodium cyanoborohydride

Product 1

HCID 15082726HCID 15082726, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a suspension of 5,10-dihydroindeno[1,2-b]indole 9.16 g, 93 mmol in glacial acetic acid (300 cm3) was added portionwise over half an hour, sodium cyanoborohydride (24 g, 400 mmol). The mixture was stirred for 3 hours, until all the material had dissolved. The solution was poured into ice water (500 cm3) and stirred for 1 hour to break down the borohydride complex. The clear solution was carefully neutralised with sodium hydroxide causing a white precipitate to form. This was filtered and washed with water until the washings were free from cyanide ion. Drying yielded the title compound as a white solid. Yield: 19 g, (98%). M.p. 107° C. 1H NMR (CDCl3) δ: 3.20 (1H, dd,), 3.51 (1H, dd), 3.99 1H, br,) 4.18 (1H, ddd,), 5.25 (1H, d), 6.60 (1H, d,), 6.74 (1H, dd,), 6.99 (1H, dd,), 7.15-7.22 (4H, m,), 7.32 (1H, d,),

Workup

  1. additionwas added portionwise over half an hour
  2. dissolutionhad dissolved
  3. stirringstirred for 1 hour
  4. customto form
  5. filtrationThis was filtered
  6. washwashed with water until the washings
  7. customDrying

Sources & evidence

ORD record
ord-a4592dfac2324c879bcb6118e3712735
Source dataset
uspto-grants-1996_05
Patent number
US05516788

Reaction notes

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