HCID 50900629, compound → HCID 50900630, compound

HRID 1921919Notes

Reaction equation

HRID 1921919 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][CH:16]=[CH:15][C:3]=1[N:4]([CH3:14])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N+:11]([O-])=O>CO.Cl[Cu]>[Cl:1][C:2]1[CH:18]=[CH:17][CH:16]=[CH:15][C:3]=1[N:4]([CH3:14])[C:5]1[C:6]([NH2:11])=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 1

HCID 50900629HCID 50900629, compound

Product 1

HCID 50900630HCID 50900630, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 887MethanolSolvent

Procedure

Compound 2 (0.121 g, 0.46 mmol) was stirred at room temperature in MeOH (4.6 mL). To this, CuCl (0.137 g, 1.38 mmol) was added and mixture stirred at room temperature for 5-10 min. KBH4 (0.174 g, 3.22 mmol) was added in portions. The reaction was stirred at room temperature until the solution became clear. The reaction was quenched with deionized H2O and extracted 3 times with 15 mL of a 90:10 mixture of ethyl acetate:dichloromethane. The organic layers were combined and dried over Na2SO4. The solvent was removed to give a brownish-black solid (107 mg, 100% yield). 1H NMR (300 MHz, CDCl3) δ 7.32 (1H, dd, J=7.8, 1.4 Hz), 7.25 (1H, dd, J=7.3, 1.7 Hz), 7.22 (1H, dd, J=7.1, 1.7 Hz), 7.16, (1H, dd, J=8.0, 1.6 Hz), 7.00-6.95 (2H, m), 6.76 (1H, ddd, J=9.3, 7.7, 1.4 Hz), 6.67 (1H, ddd, J=8.9, 7.6, 1.5 Hz); 13C (75 MHz, CDCl3) δ 147.6 (q), 142.2 (q), 136.9 (q), 130.7 (t), 130.68 (q), 127.4 (t), 125.5 (t), 123.6 (t), 121.9 (t), 118.6 (t), 115.8 (t), 41.1.

Workup

  1. stirringThe reaction was stirred at room temperature until the solution
  2. customThe reaction was quenched with deionized H2O
  3. extractionextracted 3 times
  4. additionwith 15 mL of a 90:10 mixture of ethyl acetate
  5. dry with materialdried over Na2SO4
  6. customThe solvent was removed

Sources & evidence

ORD record
ord-6475c4cfc60747bfbc7a4db86ab859fb
Source dataset
uspto-grants-2012_05
Patent number
US08173803B2

Reaction notes

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