Acetic Acid → HCID 29544554, compound

HRID 2281066Notes

Reaction equation

HRID 2281066 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) was cooled to 10° C. Cyclopropanecarboxyaldehyde (100 g, 143 mmol) was added in four 25 gram portions followed by acetic acid (300 ml, 523 mmol), which was added via addition funnel 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 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. additionwas added via addition funnel 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-dc2a7fde6bcd4a5d8d1e3d03e20cf15f
Source dataset
uspto-grants-2015_09
Patent number
US09139576B2

Reaction notes

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