Ammonia → HCID 20289480, compound

HRID 1414028Notes

Reaction equation

HRID 1414028 reaction equation
N.[O:2]=[C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:12])[N:4]1[CH2:13][CH2:14][C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([C:24]([O:26]C3C=CC([N+]([O-])=O)=CC=3)=O)[CH:22]=2)[NH:17][CH:16]=1.C[N:37](C)C=O>O>[O:2]=[C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:12])[N:4]1[CH2:13][CH2:14][C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([C:24]([NH2:37])=[O:26])[CH:22]=2)[NH:17][CH:16]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 6228DimethylformamideHCID 57206075HCID 57206075, compound

Product 1

HCID 20289480HCID 20289480, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

Ammonia (0.88, 0.2 ml) was added to a solution of 3-[2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl) ethyl]-1H-indole-5-carboxylic acid, 4-nitrophenyl ester (0.3 g) in warm (50° C.) dimethylformamide (3 ml). The mixture was stirred at 50° C. for 4 hours., poured into water (40 ml) and stirred for a further 0.5 hours. The precipitate (0.21 g) was collected and crystallised from ethanol to give the title compound (0.12 g) as an off-white solid m.p. 254°-6° C. T.L.C. Silica, Ethyl acetate:2-propanol:water:ammonia (25:15:8:2) Rf 0.75.

Workup

  1. stirringstirred for a further 0.5 hours
  2. customThe precipitate (0.21 g) was collected
  3. customcrystallised from ethanol

Sources & evidence

ORD record
ord-08740935d7fe42c9969234d13e4bd8ca
Source dataset
uspto-grants-1981_02
Patent number
US04252803

Reaction notes

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