Methyl 4-(4-(tert-butoxycarbonylamino)phenyl)-1-methyl-1H-pyrrole-2-carboxylate → Methyl 4-(4-aminophenyl)-1-methyl-1H-pyrrole-2-carboxylate

HRID 2207465Notes

Reaction equation

HRID 2207465 reaction equation
C(OC([NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[C:17]([C:21]([O:23][CH3:24])=[O:22])[N:18]([CH3:20])[CH:19]=2)=[CH:11][CH:10]=1)=O)(C)(C)C>CO.Cl.O1CCOCC1>[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[C:17]([C:21]([O:23][CH3:24])=[O:22])[N:18]([CH3:20])[CH:19]=2)=[CH:11][CH:10]=1

Participants

5

Reactant 1

HCID 67253196Methyl 4-(4-(tert-butoxycarbonylamino)phenyl)-1-methyl-1H-pyrrole-2-carboxylate

Product 1

HCID 58326676Methyl 4-(4-aminophenyl)-1-methyl-1H-pyrrole-2-carboxylate

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

5 (1 g, 3.027 mmol) was dissolved in a small volume of MeOH and 4M HCl in dioxane (15 mL) was added slowly to the stirring solution. The reaction mixture was stirred for 6 hours at which point TLC showed completion of reaction. Excess solvent was evaporated under vacuum to obtain a brown coloured solid 7. The solid product was subjected to flash chromatography (n-hexane/EtOAc 9:1) to give pure 7 (065 g, 94.2%). IR (FTIR, vmax/cm−1): 3366, 2987, 1688, 1629, 1566, 1422, 1372, 1262, 1181, 1103, 1067, 951, 821, 784, 756; 1H-NMR (400 MHz, CDCl3): δ 7.28 (2H, d, J=8.4 Hz), 7.11 (1H, d, J=2.0 Hz), 6.96 (1H, d, J=2.0 Hz), 6.68 (d, 2H, J=8.0 Hz), 3.94 (s, 3H), 3.83 (s, 3H); 13C-NMR (100 MHz, CDCl3): δ 161.7, 144.7, 126.2, 125.4, 125.2, 115.5, 114.4, 51.0, 36.8; EIMS m/z (+EI) calc. for C13H14N2O2 (M)+ 230.26. found 231.1 (M+H)+.

Workup

  1. additionwas added slowly to the stirring solution
  2. customcompletion of reaction
  3. customExcess solvent was evaporated under vacuum

Sources & evidence

ORD record
ord-05692508be7d4d4a9c9a47de86fbbd89
Source dataset
uspto-grants-2016_06
Patent number
US09376440B2

Reaction notes

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