Hydrochloric Acid → 2,5-Diphenyl-pyrrol-1-ylamine

HRID 1265286Notes

Reaction equation

HRID 1265286 reaction equation
C(OC(=O)[NH:7][N:8]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:11][CH:10]=[C:9]1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)(C)(C)C.Cl>CO>[C:13]1([C:12]2[N:8]([NH2:7])[C:9]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)=[CH:10][CH:11]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69947292(2,5-Diphenyl-pyrrol-1-yl)-carbamic acid tert-butyl ester

Product 1

HCID 44562452,5-Diphenyl-pyrrol-1-ylamineYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of (2,5-Diphenyl-pyrrol-1-yl)-carbamic acid tert-butyl ester (3.7 g, 11.06 mmol) in anhydrous methanol (25 mL) was cooled to 0° C. in an ice water bath, then treated with conc. HCl (9.86 mL). The ice bath was removed, and the resulting suspension was heated to reflux in an oil bath for 1.5 h. Upon cooling to rt, a white solid precipitated, which was filtered, washed with water and dried in vacuo to afford 2,5-Diphenyl-pyrrol-1-ylamine (2.32 g, 90%): 1H NMR (CDCl3, chemical shifts in ppm relative to TMS): 3.64 (bs, 2H), 6.28 (s, 2H), 7.28-7.33 (m, 2H), 7.42 (t, 4H, J=8.0 Hz), 7.58 (d, 4H, J=8.0 Hz).

Workup

  1. customThe ice bath was removed
  2. temperaturethe resulting suspension was heated
  3. temperatureto reflux in an oil bath for 1.5 h
  4. temperatureUpon cooling to rt
  5. customa white solid precipitated
  6. filtrationwhich was filtered
  7. washwashed with water
  8. customdried in vacuo

Sources & evidence

ORD record
ord-a6661a49486f411aad3d5d67b7fa559c
Source dataset
uspto-grants-2003_04
Patent number
US06545108B1

Reaction notes

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