Triethylamine → HCID 13713867, compound

HRID 651915Notes

Reaction equation

HRID 651915 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16](=[O:17])[C:15]3[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=3[C:9]2=[O:18])=[CH:4][C:3]=1[N+:19]([O-:21])=[O:20].Cl.[CH3:23][O:24][C:25](=[O:28])[CH2:26][NH2:27].C(N(CC)CC)C.O1CCOCC1>C(OCC)(=O)C.O>[CH3:23][O:24][C:25]([CH2:26][NH:27][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16](=[O:17])[C:15]3[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=3[C:9]2=[O:18])=[CH:4][C:3]=1[N+:19]([O-:21])=[O:20])=[O:28]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 312751,4-DioxaneHCID 122755Glycine methyl ester hydrochlorideHCID 13713866HCID 13713866, compound

Product 1

HCID 13713867HCID 13713867, compoundYield 36.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-(4-Fluoro-3-nitrophenyl)-4,5,6,7-tetrahydro-2H-isoindole-1,3-dione (5.8 g) was added to a mixture of glycine methyl ester hydrochloride (7.5 g), triethylamine (6 g) and 1,4-dioxane (50 ml), and the resultant mixture was heated under reflux for 4 hours, followed by addition of water and extraction with ethyl acetate. The extract was washed with water, dried and concentrated. The residue was crystallized from methanol to give 2-(4-methoxycarbonylmethylamino-3-nitrophenyl)-4,5,6,7-tetrahydro-2H-isoindole-1,3-dione (2.6 g). m.p., 220° C.

Workup

  1. temperatureunder reflux for 4 hours
  2. washThe extract was washed with water
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was crystallized from methanol

Sources & evidence

ORD record
ord-fee8eb0488f7433dbe9bb760b7c8b59f
Source dataset
uspto-grants-1987_06
Patent number
US04670042

Reaction notes

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