Hydrochloric Acid → 3,5-Dimethyl-4-propyl-1H-pyrrole-2-carboxylic acid ethyl ester

HRID 1834431Notes

Reaction equation

HRID 1834431 reaction equation
Cl.[CH3:2][C:3]1[NH:4][C:5]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:6]([CH3:8])[CH:7]=1.[CH:14](=O)[CH2:15][CH3:16]>[Zn].C(OC(=O)C)(=O)C>[CH3:2][C:3]1[NH:4][C:5]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:6]([CH3:8])[C:7]=1[CH2:14][CH2:15][CH3:16]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 527PropanalHCID 1374771H-Pyrrole-2-carboxylic acid, 3,5-dimethyl-, ethyl ester

Product 1

HCID 1383463,5-Dimethyl-4-propyl-1H-pyrrole-2-carboxylic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 7918Acetic AnhydrideSolvent

Procedure

Acetic anhydride (20 ml) was added to stirred and cooled concentrated hydrochloric acid (5 ml), and 2,4-dimethyl-5-carbethoxy-pyrrole (0.668 g) was dissolved in this. Propionaldehyde (0.6 ml) and amalgamated zinc (10 g, 20 mesh) was added, the mixture stirred 15 min, at 20°-25° then decanted into ice water (100 ml). The solid was distilled (80°-95°, 1 × 10-4 mm) and crystallized from aqueous ethanol as colourless irregular prisms (48%), m.p. 99°-99.5° (lit19) 98°). Anal. Calc. for C12H19NO2 : C, 68.86; H, 9.15; N, 6.69. Found: C, 68.75; H, 9.19; N, 6.89.

Workup

  1. dissolutionwas dissolved in this
  2. stirringthe mixture stirred 15 min, at 20°-25°
  3. customthen decanted into ice water (100 ml)
  4. distillationThe solid was distilled (80°-95°, 1 × 10-4 mm)
  5. customcrystallized from aqueous ethanol as colourless irregular prisms (48%), m.p. 99°-99.5° (lit19) 98°)

Sources & evidence

ORD record
ord-6adafcaa62e94c368a90d43fe814e942
Source dataset
uspto-grants-1978_01
Patent number
US04070366

Reaction notes

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