3-Chloroaniline → HCID 18663372, compound

HRID 1956686Notes

Reaction equation

HRID 1956686 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[C:9]([O:13][C:14]([NH:16][CH:17]([CH2:20][C:21]#[C:22][CH3:23])[CH:18]=O)=[O:15])([CH3:12])([CH3:11])[CH3:10].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].CCOC(C)=O>ClC(Cl)C>[C:9]([O:13][C:14]([NH:16][CH:17]([CH2:20][C:21]#[C:22][CH3:23])[CH2:18][NH:5][C:4]1[CH:6]=[CH:7][CH:8]=[C:2]([Cl:1])[CH:3]=1)=[O:15])([CH3:12])([CH3:11])[CH3:10]

Participants

6

Reactant 4

HCID 79323-ChloroanilineHCID 8857Ethyl AcetateHCID 5049666Sodium triacetoxyborohydrideHCID 45092115HCID 45092115, compound

Product 1

HCID 18663372HCID 18663372, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a 0° C. solution of 3-chloroaniline (4.33 mL, 40.9 mmol), the product from Step K (ca. 41 mmol), and crushed 4 Å molecular sieves (10 g) in dichloroethane (100 mL) under nitrogen was added sodium triacetoxyborohydride (12.9 g, 61.5 mmol). The reaction was stirred for one hour, then warmed to room temperature. After 3 hours, the solution was poured into EtOAc and washed with water, sat. NaHCO3 soln. and brine. The solution was dried over sodium sulfate and concentrated in vacuo to provide the crude product.

Workup

  1. waitAfter 3 hours
  2. washwashed with water, sat. NaHCO3 soln
  3. dry with materialThe solution was dried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1091ce6b8c374d6cb8f3f4569d03fb08
Source dataset
uspto-grants-1998_07
Patent number
US05780492

Reaction notes

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