Dimethylformamide → HCID 21569617, compound

HRID 1579909Notes

Reaction equation

HRID 1579909 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[CH2:15][CH2:14][C:13]4[CH:17]=[CH:18][CH:19]=[CH:20][C:12]=4[C:11]=3[CH:10]=[C:9]2[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:4][C:3]=1[C:27](OC)=O.[OH-:31].[NH4+:32].CN(C)C=O>O>[C:27]([C:3]1[CH:4]=[C:5]([N:8]2[C:16]3[CH2:15][CH2:14][C:13]4[CH:17]=[CH:18][CH:19]=[CH:20][C:12]=4[C:11]=3[CH:10]=[C:9]2[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:6]=[CH:7][C:2]=1[OH:1])(=[O:31])[NH2:32]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 14923Ammonium HydroxideHCID 122703174,5-Dihydro-3-(4-hydroxy-3-methoxycarbonylphenyl)2-phenylbenz[e]indole

Product 1

HCID 21569617HCID 21569617, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2.0 g. (0.005 mole) of 4,5-dihydro-3-(4-hydroxy-3-methoxycarbonylphenyl)2-phenylbenz[e]indole, 75 ml. of ammonium hydroxide, and 40 ml. of dimethyl formamide was heated under reflux for 3 hours, cooled, diluted with water, acidified, and extracted with ether. The ether phase was dried over sodium sulfate and concentrated to a solid. Recrystallization from benzene gave 1.21 g. (63%) of colorless crystals, m.p. 213°-215°.

Workup

  1. additionA mixture of 2.0 g
  2. temperatureunder reflux for 3 hours
  3. temperaturecooled
  4. extractionextracted with ether
  5. dry with materialThe ether phase was dried over sodium sulfate
  6. concentrationconcentrated to a solid
  7. customRecrystallization from benzene
  8. customgave 1.21 g

Sources & evidence

ORD record
ord-93b1c71a3a564c96b784e222b09b521f
Source dataset
uspto-grants-1976_01
Patent number
US03931407

Reaction notes

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