Dichloromethane → HCID 18706970, compound

HRID 1422071Notes

Reaction equation

HRID 1422071 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:16]([CH2:30][CH3:31])=[C:17]3[CH:25]=[CH:24][CH:23]=[C:22]4[N:18]3[C:19]=2[CH:20]=[C:21]4[C:26]([O:28]C)=[O:27])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].ClCCl>CO.O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:16]([CH2:30][CH3:31])=[C:17]3[CH:25]=[CH:24][CH:23]=[C:22]4[N:18]3[C:19]=2[CH:20]=[C:21]4[C:26]([OH:28])=[O:27])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 14797Potassium HydroxideHCID 11144022HCID 11144022, compound

Product 1

HCID 18706970HCID 18706970, compoundYield 26.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

Methyl 3-(4-benzyloxyphenyl)-4-ethylpyrrolo[2,1,5-cd]indolizine-1-carboxylate (2.92 g, 7.13 mmol) was dissolved in 200 ml of methanol and 20 ml of water. Potassium hydroxide (6.40 g, 114 mmol) was added and the mixture was heated to reflux for 3 days. The reaction mixture was allowed to cool to room temperature and the methanol was evaporated. The orange solid was partitioned between 200 ml of dichloromethane and 200 ml of 1M hydrochloric acid and acidified with concentrated hydrochloric acid until pH=1. This resulted in the formation of a suspension. A further 800 ml of dichloromethane and 200 ml of water was added and the suspension was filtered to give 0.74 g (26%) of 3-(4-benzyloxyphenyl)-4-ethylpyrrolo[2,1,5-cd]indolizine-1-carboxylic acid as a yellow solid. The organic solution was washed with brine, dried over magnesium sulfate and evaporated to give a orange solid. This solid was recrystallised from acetone to afford 1.23 g (43%) of 3-(4-benzyloxyphenyl)-4-ethylpyrrolo[2,1,5-cd]indolizine-1-carboxylic acid as a yellow solid. M.p. 223-224° C. MS(SP): m/z 395 (M+). 1H-NMR (DMSO-d6, 200 MHz) δ: 1.41 (t, 3H); 3.02 (q, 2H); 5.22 (s, 2H); 7.24 (d, 2H); 7.31-7.56 (m, 5H); 7.81 (d, 2H); 7.95 (t, 1H); 8.03 (s, 1H); 8.20 (d, 1H); 8.32 (d, 1H); 12.46 (bs, 1H).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 3 days
  3. customthe methanol was evaporated
  4. customThe orange solid was partitioned between 200 ml of dichloromethane and 200 ml of 1M hydrochloric acid
  5. customThis resulted in the formation of a suspension
  6. filtrationthe suspension was filtered

Sources & evidence

ORD record
ord-71a4bf4dbba74c668deb1f9ca2e2ceed
Source dataset
uspto-grants-2000_06
Patent number
US06080754

Reaction notes

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