Sodium Hydroxide → HCID 53966542, compound

HRID 439870Notes

Reaction equation

HRID 439870 reaction equation
[CH3:1][C:2]1[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[C:14]2[C:3]=1[CH2:4][C:5]1[NH:6][C:7]3[C:12]([C:13]=12)=[CH:11][CH:10]=[CH:9][CH:8]=3.[BH3-]C#N.[Na+].[OH-].[Na+]>C(O)(=O)C.O>[CH3:1][C:2]1[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[C:14]2[C:3]=1[CH2:4][C@@H:5]1[C@H:13]2[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6]1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 22408474HCID 22408474, compound

Product 1

HCID 53966542HCID 53966542, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a stirred suspension of 0.74 g of (0.00296 mol) of 5,6-dihydro-7-methyl-9-methoxyindeno[2,1-b]indole in 25 ml of acetic acid was added 0.93 g (0.0148 mol) of NaCNBH3 in portions during 5 minutes. The mixture was stirred for 3 hours at room temperature, whereafter it was diluted with water and then stirred for another hour. The resulting mixture was alkalinized with NaOH-solution (10M) to pH9, and was then extracted twice with ether. The combined organic phases were washed twice with aqueous NaCl-solution and dried (Na2SO4). After evaporation the residue was purified by chromatography on silica using methylene chloride as eluant. This gave 0.61 g (24%) of the expected product. M.p. 104° C. 1H NMR (CDCl3): 2.2 (3H,s), 3.0-3.4 (2H,dd), 3.4-3.5 (1H,bs), 3.75 (3H,s), 4.65-4.80 (2H,m), 6.4-7.4 (6H,m)--thereof 6.45 (1H,dd), 6.75 (1H,dd).

Workup

  1. stirringstirred for another hour
  2. extractionwas then extracted twice with ether
  3. washThe combined organic phases were washed twice with aqueous NaCl-solution
  4. dry with materialdried (Na2SO4)
  5. customAfter evaporation the residue
  6. customwas purified by chromatography on silica

Sources & evidence

ORD record
ord-94e9b2b2f92c48249f4f99abf71e1223
Source dataset
uspto-grants-1996_05
Patent number
US05516788

Reaction notes

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