Sulfuric Acid → HCID 13464802, compound

HRID 1443909Notes

Reaction equation

HRID 1443909 reaction equation
N[N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3]1.[C:11]1(=O)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.S(=O)(=O)(O)O>O>[CH:8]1[CH:7]=[CH:6][C:5]2[CH2:4][CH2:3][N:2]3[C:10]=2[C:9]=1[C:11]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][C:12]=13

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 10400CycloheptanoneHCID 27609322,3-dihydro-1H-indol-1-amine

Product 1

HCID 13464802HCID 13464802, compoundYield 29.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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-41b62b6de69944508d3ef29e2db73281
Source dataset
uspto-grants-2010_02
Patent number
US07662831B2

Reaction notes

Loading…