Ethyl chloroformate → Ethyl 6-nitro-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indole-2-carboxylate

HRID 735198Notes

Reaction equation

HRID 735198 reaction equation
[N+:1]([C:4]1[C:12]2[NH:11][C:10]3[CH2:13][CH2:14][NH:15][CH2:16][C:9]=3[C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH2:17]([O:19][C:20](Cl)=[O:21])[CH3:18]>C(Cl)Cl.C([O-])([O-])=O.[K+].[K+]>[CH2:17]([O:19][C:20]([N:15]1[CH2:14][CH2:13][C:10]2[NH:11][C:12]3[C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=[CH:7][C:8]=3[C:9]=2[CH2:16]1)=[O:21])[CH3:18]

Participants

5

Reactant 2

HCID 10928Ethyl chloroformateHCID 688159346-nitro-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

Product 1

HCID 68819808Ethyl 6-nitro-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indole-2-carboxylateYield 56%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 11430Potassium CarbonateSolvent

Procedure

6-Nitro-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (250 mg, 0.99 mmol) was dissolved in CH2Cl2 (2.5 mL) with sat. aq. K2CO3. Ethylchloroformate (130 mg, 1.2 mmol) was added at 0° C. The reaction was brought to room temperature and stirred for 15 h. The layers were separated and the aqueous layer was extracted with CHCl3 (3×5 mL). The combined extracts were washed with brine (10 mL), dried (MgSO4) and evaporated affording ethyl-6-nitro-1,3,4,5-tetrhydro-2H-pyrido[4,3-b]indole-2-carboxylate as an orange semi-solid (160 mg, 56%). 1H NMR (CDCl3, 300 MHz) δ 8.17 (d, 1H, J=8.1 Hz), 7.78 (d, 1H, J=7.6 Hz), 3.19 (t, 1H, J=8.1 Hz), 4.73 (s, 2H), 4.18-4.23 (m, 4H), 2.91-2.98 (m, 2H), 1.30-1.39 (t, 3H, J=6.9 Hz) ppm.

Workup

  1. customwas brought to room temperature
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with CHCl3 (3×5 mL)
  4. washThe combined extracts were washed with brine (10 mL)
  5. dry with materialdried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-4276d4c13f4043c587e3fa884f0dae2a
Source dataset
uspto-grants-2009_09
Patent number
US07592454B2

Reaction notes

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