Hydrochloric Acid → 4-(1-Ethylpyrrolo[2,1,5-cd]indolizin-2-yl)phenol

HRID 1421269Notes

Reaction equation

HRID 1421269 reaction equation
[CH2:1]([C:3]1[C:11]2[N:6]3[C:7](=[CH:12][CH:13]=[C:5]3[C:4]=1[C:14]1[CH:19]=[CH:18][C:17]([O:20]C)=[CH:16][CH:15]=1)[CH:8]=[CH:9][CH:10]=2)[CH3:2].[Cl-].[Al+3].[Cl-].[Cl-].C(S)C.Cl>ClCCl.C1(C)C=CC=CC=1.C(OCC)(=O)C.C(OCC)(=O)C.O.O1CCCC1>[CH2:1]([C:3]1[C:11]2[N:6]3[C:7](=[CH:12][CH:13]=[C:5]3[C:4]=1[C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1)[CH:8]=[CH:9][CH:10]=2)[CH3:2]

Participants

10

Reactant 4

HCID 313Hydrochloric AcidHCID 6343EthanethiolHCID 6451240Aluminum(III) ChlorideHCID 18706925HCID 18706925, compound2×

Product 1

HCID 99033364-(1-Ethylpyrrolo[2,1,5-cd]indolizin-2-yl)phenolYield 44%

Reagents, catalysts & solvents 5

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 21584019Toluene ethylacetateSolvent

Procedure

A solution of 1-ethyl-2-(4-methoxyphenyl)pyrrolo[2,1,5-cd]indolizine (Compound 34) (0.77 g, 2.79 mmol) in 25 ml of dry dichloromethane was stirred under a nitrogen atmosphere and aluminium chloride (2.23 g, 16.7 mmol) was added in portions. When the addition was complete, ethanethiol (1.25 ml, 16.7 mmol) was added, and stirring was continued for half an hour. The mixture was cooled in an ice bath followed by the addition of tetrahydrofuran (15 ml), 6M hydrochloric acid (3 ml), water (50 ml) and ethyl acetate (100 ml). The organic phase was separated and evaporated to leave a residue which was chromatograped over silica gel with toluene/ethyl acetate (4:1) as eluent. The proper fractions were collected and evaporated, and the residue was triturated with a mixture of ether (2 ml) and petroleum ether (5 ml) to afford 0.32 g (44%) of the title compound. M.p. 104-05° C. 1H-NMR (DMSO-d6, 200 MHz) δ: 1.41 (t, 3H), 3.22 (q, 2H), 6.98 (d, 2H), 7.29 (d, 1H), 7.67 (d, 2H), 7.69(d, 1H), 7.72(t, 1H), 8.05 (d, 1H), 8.10 (d, 1H), 9.68 (s, 1H). (Compound 52).

Workup

  1. additionWhen the addition
  2. waitwas continued for half an hour
  3. temperatureThe mixture was cooled in an ice bath
  4. customThe organic phase was separated
  5. customevaporated
  6. customto leave a residue which
  7. customThe proper fractions were collected
  8. customevaporated
  9. customthe residue was triturated with a mixture of ether (2 ml) and petroleum ether (5 ml)

Sources & evidence

ORD record
ord-a374bcabcbc34a1ba1af58cf0c0f7be5
Source dataset
uspto-grants-2000_06
Patent number
US06075036

Reaction notes

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