Hydrochloric Acid → HCID 59004602, compound

HRID 1668495Notes

Reaction equation

HRID 1668495 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([C:8]([C:13]3[CH2:22][CH2:21][C:16]4(OCC[O:17]4)[CH2:15][CH:14]=3)=[CH:9][NH:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl>CC(C)=O>[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([C:8]([C:13]3[CH2:22][CH2:21][C:16](=[O:17])[CH2:15][CH:14]=3)=[CH:9][NH:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 590046416-Nitro-3-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)-1H-indole

Product 1

HCID 59004602HCID 59004602, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of compound 118 (3.9 g, 12.986 mmol) in acetone (50 mL) was treated with 10% aq. HCl (50 mL) at room temperature and stirred for over night (14 h). Solvent was evaporated and crude was basified using 10% aq. NH4OH solution (100 mL). The solid was filtered off, washed with 10% NH4OH solution (20 mL), water (2×15 mL) and dried under vacuum to obtain compound 119 (2.81 g, 85%) as a yellow solid. mp 175-177° C.; 1H NMR (DMSO-d6) δ 2.58 (t, 2H, J=6.9 Hz), 2.90 (t, 2H, J=6.9 Hz), 3.04-3.10 (m, 2H), 6.24 (t, 1H, J=3.9 Hz), 7.90-8.01 (m, 3H), 8.33 (d, 1H, J=2.1 Hz), 11.95 (s, 1H); ESI-MS (m/z, %): 279 (M+Na, 100), 257 (MH+, 33).

Workup

  1. customSolvent was evaporated
  2. filtrationThe solid was filtered off
  3. washwashed with 10% NH4OH solution (20 mL), water (2×15 mL)
  4. customdried under vacuum

Sources & evidence

ORD record
ord-bc61de3fec694192978b518fdefcf144
Source dataset
uspto-grants-2011_08
Patent number
US07989447B2

Reaction notes

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