3-(3-Methoxy-5,6,7,8-tetrahydronaphthalen-2-yl)-2-azido-2-propenoic acid ethyl ester → 2-Carboethoxy-4-methoxy-6,7,8,9-tetrahydro-1h-benz[g]indole

HRID 489108Notes

Reaction equation

HRID 489108 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[C:5]([N:19]=[N+]=[N-])=[CH:6][C:7]1[C:16]([O:17][CH3:18])=[CH:15][C:14]2[CH2:13][CH2:12][CH2:11][CH2:10][C:9]=2[CH:8]=1)[CH3:2]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O.[Rh+2].[Rh+2]>[C:4]([C:5]1[NH:19][C:8]2[C:7]([CH:6]=1)=[C:16]([O:17][CH3:18])[CH:15]=[C:14]1[CH2:13][CH2:12][CH2:11][CH2:10][C:9]=21)([O:3][CH2:1][CH3:2])=[O:22]

Participants

4

Reactant 1

HCID 730806763-(3-Methoxy-5,6,7,8-tetrahydronaphthalen-2-yl)-2-azido-2-propenoic acid ethyl ester

Product 1

HCID 111848862-Carboethoxy-4-methoxy-6,7,8,9-tetrahydro-1h-benz[g]indoleYield 83,533.102%

Reagents, catalysts & solvents 2

HCID 152122Dirhodium tetraacetateCatalystHCID 1140TolueneSolvent

Procedure

A solution of 3-(3-methoxy-5,6,7,8-tetrahydronaphthalen-2-yl)-2-azido-2-propenoic acid ethyl ester (34.2 g, 0.113 mmol) in toluene (200 mL) was treated with rhodium(II) acetate dimer (300 mg, 0.679 mmol) at 95° C. for 4 h then at reflux for 1 h. The mixture was cooled to room temperature and the resulting solids were collected via vacuum filtration. The filtrate was concentrated to give a further precipitate that was collected via vacuum filtration. The filtrate was filtered through a silica gel plug and concentrated to provide an additional portion of product to give a total of 25.8 g (83%) of the title compound: mp 202-203° C. 1H NMR (CDCl3) δ 8.65 (bs, 1H, —NH), 7.30 (d, J=2.2 Hz, 1H), 6.24 (s, 1H), 4.38 (q, J=7.0 Hz, 2H), 3.91 (s, 3H), 2.84 (t, J=5.9 Hz, 2H), 2.76 (t, J=5.5 Hz, 2H), 1.90 (m, 4H), 1.40 (t, J=7.0 Hz, 3H); MS ES+ m/e 274 (p+1); IR (CHCl3, cm−1) 3459, 2937, 1698.

Workup

  1. temperatureat reflux for 1 h
  2. filtrationthe resulting solids were collected via vacuum filtration
  3. concentrationThe filtrate was concentrated
  4. customto give a further precipitate that
  5. filtrationwas collected via vacuum filtration
  6. filtrationThe filtrate was filtered through a silica gel plug
  7. concentrationconcentrated
  8. customto provide an additional portion of product

Sources & evidence

ORD record
ord-bd141e3f96354a4781c43bd0dde48ee0
Source dataset
uspto-grants-2005_12
Patent number
US06974831B2

Reaction notes

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