Methylamine → 3,9b-Dimethyl-3a-hydroxy-8-methoxy-2-oxo-2,3,3a,4,5,9b-hexahydro-1H-benz[e]indole

HRID 224965Notes

Reaction equation

HRID 224965 reaction equation
C([O:3][C:4](=O)[CH2:5][C:6]1([CH3:19])[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:16][CH3:17])[CH:14]=2)[CH2:9][CH2:8][C:7]1=[O:18])C.[CH3:21][NH2:22]>C(O)C>[CH3:21][N:22]1[C:7]2([OH:18])[C:6]([CH3:19])([C:15]3[CH:14]=[C:13]([O:16][CH3:17])[CH:12]=[CH:11][C:10]=3[CH2:9][CH2:8]2)[CH2:5][C:4]1=[O:3]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 54480711Ethyl 7-methoxy-1-methyl-2-oxo-1,2,3,4-tetrahydro-1-naphthaleneacetate

Product 1

HCID 233307903,9b-Dimethyl-3a-hydroxy-8-methoxy-2-oxo-2,3,3a,4,5,9b-hexahydro-1H-benz[e]indole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 22.0 g (79.7 mmol) ethyl-7-methoxy-1-methyl-2-oxo-1,2,3,4-tetrahydro-1-naphthaleneacetate (IXb) and 7.5 g (240 mmol) methylamine in 25 ml ethanol was left at room temperature for 24 hr. The crystalline precipitate formed was separated to give 15.5 g (74.5%) Xb, m.p. 182°-186°. From the mother liquor, after evaporation (35°) and treatment with ether, 1.0 g, additional Xb was collected increasing the yield to 79.5%; IR (Nujol), 3300 (OH), 1670 cm-1 (lactam); NMR (CDCl3 -DMSO) δ, 1.48 (s, 3, CH3), 2.82 (s, 3, N-CH3), 3.78 (s, 3, OCH3), 6.6-7.1 (m, 3, ArH).

Workup

  1. customThe crystalline precipitate formed
  2. customwas separated
  3. customto give 15.5 g (74.5%) Xb, m.p. 182°-186°
  4. customFrom the mother liquor, after evaporation (35°) and treatment with ether, 1.0 g, additional Xb
  5. customwas collected
  6. temperatureincreasing the
  7. customyield to 79.5%

Sources & evidence

ORD record
ord-1a7f72add6b54b85ab3b6ed613a73121
Source dataset
uspto-grants-1980_11
Patent number
US04234731

Reaction notes

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