Hydrochloric Acid → 7Benzyloxy-3-(4-benzyloxyphenyl)-4-ethylpyrrolo[2,1,5-cd]indolizine-1,2-dicarboxylic acid

HRID 1422078Notes

Reaction equation

HRID 1422078 reaction equation
[CH2:1]([O:8][C:9]1[C:17]2[N:13]3[C:14]([C:26]([C:30]4[CH:35]=[CH:34][C:33]([O:36][CH2:37][C:38]5[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=5)=[CH:32][CH:31]=4)=[C:27]([CH2:28][CH3:29])[C:12]3=[CH:11][CH:10]=1)=[C:15]([C:22]([O:24]C)=[O:23])[C:16]=2[C:18]([O:20]C)=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].O.Cl>CO>[CH2:1]([O:8][C:9]1[C:17]2[N:13]3[C:14]([C:26]([C:30]4[CH:31]=[CH:32][C:33]([O:36][CH2:37][C:38]5[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=5)=[CH:34][CH:35]=4)=[C:27]([CH2:28][CH3:29])[C:12]3=[CH:11][CH:10]=1)=[C:15]([C:22]([OH:24])=[O:23])[C:16]=2[C:18]([OH:20])=[O:19])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14797Potassium HydroxideHCID 18707022Dimethyl 7-benzyloxy-3-(4-benzyloxyphenyl)-4-ethylpyrrolo[2,1,5-cd]indolizine-1,2-dicarboxylate

Product 1

HCID 187069227Benzyloxy-3-(4-benzyloxyphenyl)-4-ethylpyrrolo[2,1,5-cd]indolizine-1,2-dicarboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dimethyl 7-Benzyloxy-3-(4-benzyloxyphenyl)-4-ethylpyrrolo[2,1,5-cd]indolizine-1,2-dicarboxylate (1.0 g, 1.7 mmol) was dissolved in 100 ml of methanol. Potassium hydroxide (3.37 g, 60 mmol) and 2 ml of water was added and the mixture was heated to reflux for 4 days. The reaction mixture was allowed to cool to room temperature and acidified with concentrated hydrochloric acid until pH=1. The resulting precipitate was filtered off, and washed with water and ethanol. This gave 0.89 g (96%) of 7-benzyloxy-3-(4-benzyloxyphenyl)-4-ethylpyrrolo[2,1,5-cd]indolizine-1,2-dicarboxylic acid as yellow crystals. M.p. 151-161° C. MS(SP): m/z 545 (M+). 1H-NMR (DMSO-d6, 200 MHz) δ: 1.32 (t, 3H); 3.02 (q, 2H); 5.18 (s, 2H); 5.52 (s, 2H); 7.15 (d, 2H); 7.29-7.56 (m, 10H); 7.61-7.71 (m, 3H); 8.18 (d, 1H).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 4 days
  3. filtrationThe resulting precipitate was filtered off
  4. washwashed with water and ethanol

Sources & evidence

ORD record
ord-2b8667c3e7ba412a84aa66450cdf7bce
Source dataset
uspto-grants-2000_06
Patent number
US06080754

Reaction notes

Loading…