Acetic Acid → HCID 29544554, compound

HRID 2281031Notes

Reaction equation

HRID 2281031 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[C:5]([N+:10]([O-:12])=[O:11])[CH:4]=1.[C:13](O)(=O)[CH3:14].[C:17](O[BH-](OC(=O)C)OC(=O)C)(=O)[CH3:18].[Na+].C(=O)(O)[O-].[Na+]>ClCCl>[CH:13]1([CH2:14][NH:7][C:6]2[CH:8]=[CH:9][C:3]([O:2][CH3:1])=[CH:4][C:5]=2[N+:10]([O-:12])=[O:11])[CH2:18][CH2:17]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 667934-Methoxy-2-nitroanilineHCID 516892Sodium Bicarbonate2×HCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 29544554HCID 29544554, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
10 °C

Procedure

A 5 L vessel was charged 4-methoxy-2-nitroaniline (160 g, 952 mmol) in dichloromethane (2.44 L). The mixture was cooled to 10° C. and cyclopropanecarboxyaldehyde (100 g, 143 mmol) was added in four 25 gram portions. The vessel was charged with acetic acid (300 ml, 523 mmol) via an addition funnel and charged to the reaction mixture over 20 minutes. After 45 minutes, the vessel was charged with sodium triacetoxyborohydride (444 g, 209 mmol) portionwise. The mixture was warmed to ambient temperature over 4 hours and was stirred for an additional 14 hours. The mixture was treated with saturated aqueous sodium bicarbonate (100 mL) and poured into sodium bicarbonate (4 L) and dichloromethane. The organic extract was concentrated in vacuo, providing the titled compound.

Workup

  1. additioncharged to the reaction mixture over 20 minutes
  2. temperatureThe mixture was warmed to ambient temperature over 4 hours
  3. extractionThe organic extract
  4. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-7e12bc26b1b249ba94d3ce0413febb6e
Source dataset
uspto-grants-2015_09
Patent number
US09139576B2

Reaction notes

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