3,4-Diaminobenzophenone → HCID 22458410, compound

HRID 2185508Notes

Reaction equation

HRID 2185508 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1[NH2:16])[C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:6].[BH4-].[Na+]>CO>[OH:6][CH:5]([C:4]1[CH:13]=[CH:14][C:15]([NH2:16])=[C:2]([NH2:1])[CH:3]=1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 1355203,4-DiaminobenzophenoneHCID 4311764Sodium borohydride

Product 1

HCID 22458410HCID 22458410, compoundYield 91.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
0 °C

Procedure

3,4-Diaminobenzophenone (5.79 g, 27 mmol) was dissolved in MeOH (80 mL) and cooled to 0° C. A solution of NaBH4 (4.12 g, 109 mmol) in MeOH (30 mL) was added dropwise over 10 min. The mixture was stirred for 2 hours and concentrated to dryness. The residue was dissolved in EtOAc and washed with NaHCO3 (3×50 mL). The organic layer was dried over Na2SO4, filtered and concentrated to afford the title compound (5.3 g, 90%): 1HNMR (400 MHz, CDCl3) δ 5.6-5.65 (1H, s), 6.6-6.7 (3H, m), 7.2-7.45 (5H, m).

Workup

  1. concentrationconcentrated to dryness
  2. dissolutionThe residue was dissolved in EtOAc
  3. washwashed with NaHCO3 (3×50 mL)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6b8fa2c926de4476892d3d0a09b06218
Source dataset
uspto-grants-2002_06
Patent number
US06399629B1

Reaction notes

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