Hydrochloric Acid → 6-Amino-3-butyl-5-nitro-phthalide

HRID 2120190Notes

Reaction equation

HRID 2120190 reaction equation
C([NH:4][C:5]1[CH:14]=[C:13]2[C:8]([CH:9]([CH2:15][CH2:16][CH2:17][CH3:18])[O:10][C:11]2=[O:12])=[CH:7][C:6]=1[N+:19]([O-:21])=[O:20])(=O)C.Cl.O>C(O)C>[NH2:4][C:5]1[CH:14]=[C:13]2[C:8]([CH:9]([CH2:15][CH2:16][CH2:17][CH3:18])[O:10][C:11]2=[O:12])=[CH:7][C:6]=1[N+:19]([O-:21])=[O:20]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 234391106-Acetamido-3-butyl-5-nitro-phthalide

Product 1

HCID 234391186-Amino-3-butyl-5-nitro-phthalide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 29.2 g of compound obtained in Step A in 25 ml of 95% ethanol there are added 15 ml of hydrochloric acid and 20 ml of water. The mixture is refluxed for 3 hours and put aside at room temperature overnight The solvents are removed under reduced pressure. The residue is treated with 5% NaOH; the solid is collected and washed with water, dried, and crystallised from ethanol giving the title compound.

Workup

  1. temperatureThe mixture is refluxed for 3 hours
  2. customThe solvents are removed under reduced pressure
  3. additionThe residue is treated with 5% NaOH
  4. customthe solid is collected
  5. washwashed with water
  6. customdried
  7. customcrystallised from ethanol giving the title compound

Sources & evidence

ORD record
ord-355a38d0f633416bb681a6a22ff48fde
Source dataset
uspto-grants-2004_02
Patent number
US06689808B2

Reaction notes

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