2-[(Bis-formyl)amino]-1-[5-(4-chlorobenzoyl)-1-methyl-1H-pyrrol-3-yl]-ethanone → 2-Amino-1-[5-(4-Chlorobenzoyl)-1-methyl-1H-pyrrol-3-yl]-ethanone hydrochloride

HRID 841040Notes

Reaction equation

HRID 841040 reaction equation
C([N:3](C=O)[CH2:4][C:5]([C:7]1[CH:11]=[C:10]([C:12](=[O:20])[C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[N:9]([CH3:21])[CH:8]=1)=[O:6])=O>Cl.CCO>[ClH:19].[NH2:3][CH2:4][C:5]([C:7]1[CH:11]=[C:10]([C:12](=[O:20])[C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[N:9]([CH3:21])[CH:8]=1)=[O:6]

Participants

3

Reactant 1

HCID 212566812-[(Bis-formyl)amino]-1-[5-(4-chlorobenzoyl)-1-methyl-1H-pyrrol-3-yl]-ethanone

Product 1

HCID 226208052-Amino-1-[5-(4-Chlorobenzoyl)-1-methyl-1H-pyrrol-3-yl]-ethanone hydrochloride

Reagents, catalysts & solvents 1

HCID 21887872Ethanol hydrochlorideSolvent

Procedure

6.18 g (0.0186 mole) 2-[(Bis-formyl)amino]-1-[5-(4-chlorobenzoyl)-1-methyl-1H-pyrrol-3-yl]-ethanone was stirred 3 days in 5% HCl/EtOH. A 0.5 mL portion of conc. HCL was added and the reaction stirred for two more days. The solid was collected by filtration. The solid was stirred in refluxing methanol and the undissolved solid collected by filtration and discarded. The filtrate was cooled to room temperature and diethyl ether was added. The solid was collected. It was twice treated with boiling methanol to give pure product: mp 290° C. (decomp.); mass spectrum (CH4—Cl) m/z=277 (M+1); NMR (Me2SO-d6) d 8.2 (br s, 4 H); 7.85 (d, 2 H); 7.6 (d, 2 H); 7.2 (s, 1H); 4.3 (s, 2 H); 4.0 (s 3 H). Anal Calcd for C14H13ClN2O2—HCl: C, 53.69; H, 4.51; N, 8.94. Found: C, 53.91; H, 4.4.1; N, 8.76.

Workup

  1. additionA 0.5 mL portion of conc. HCL was added
  2. filtrationThe solid was collected by filtration
  3. stirringThe solid was stirred
  4. temperaturein refluxing methanol
  5. filtrationthe undissolved solid collected by filtration
  6. additiondiethyl ether was added
  7. customThe solid was collected
  8. additionIt was twice treated with boiling methanol
  9. customto give pure product

Sources & evidence

ORD record
ord-32baab5fa04e49e8ace6025b8c5f615e
Source dataset
uspto-grants-2002_04
Patent number
US06369228B2

Reaction notes

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