Hydrochloric Acid → Nitroindoline

HRID 1443908Notes

Reaction equation

HRID 1443908 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[N:10]([O-:12])=[O:11].[Na+].Cl>O.CCOCC>[N+:10]([N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1)([O-:12])=[O:11]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 10328IndolineHCID 23668193Sodium Nitrite

Product 1

HCID 21959507NitroindolineYield 111.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

Following the procedure of Example 1, step 1, indoline (20 g, 170 mmol), sodium nitrite (14 g, 200 mmol), concentrated hydrochloric acid (30 mL) in water (70 mL) and ether (120 mL) provided 1-nitroindoline (31 g), which was reduced with zinc dust (˜50 g) in acetic acid (500 mL) to provide 1-aminoindoline (29 g). A mixture of 1-aminoindoline (17 g, 130 mmol), cycloheptanone (15 mL, 130 mmol), and concentrated sulfuric acid (20 mL) in water (180 mL) provided 8.2 g of 4,5,8,9,10,11-hexahydro-7H-cyclohepta[b]pyrrolo[3,2,1-hi]indole. MS (ESI) m/z 212.

Sources & evidence

ORD record
ord-a7bcd3676cf742f2b3023141617642a7
Source dataset
uspto-grants-2010_02
Patent number
US07662831B2

Reaction notes

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