Toluene → 6-Cyano-3-(3,5-dibromo-4-hydroxy-benzylidene)-1,3-dihydro-indol-2-one

HRID 1387421Notes

Reaction equation

HRID 1387421 reaction equation
[C:1]([C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][C:8](=[O:12])[NH:9]2)=[CH:5][CH:4]=1)#[N:2].[Br:13][C:14]1[CH:15]=[C:16]([CH:19]=[C:20]([Br:23])[C:21]=1[OH:22])[CH:17]=O.C1(C)C=CC=CC=1>O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>[C:1]([C:3]1[CH:11]=[C:10]2[C:6]([C:7](=[CH:17][C:16]3[CH:15]=[C:14]([Br:13])[C:21]([OH:22])=[C:20]([Br:23])[CH:19]=3)[C:8](=[O:12])[NH:9]2)=[CH:5][CH:4]=1)#[N:2]

Participants

6

Reactant 3

HCID 1140TolueneHCID 181003,5-Dibromo-4-HydroxybenzaldehydeHCID 27733482-Oxindole-6-carbonitrile

Product 1

HCID 542091966-Cyano-3-(3,5-dibromo-4-hydroxy-benzylidene)-1,3-dihydro-indol-2-oneYield 65.7%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 962WaterSolvent

Procedure

6-cyano-1,3-dihydro-indol-2-one (46.3 mg, 0.29 mmol) and 3,5-dibromo-4-hydroxybenzaldehyde (80 mg, 0.39 mmol) and p-toluenesulfonic acid monohydrate (1 mg, 0.005 mmol) were treated with toluene (30 mL) and the reaction refluxed with stirring with a Dean-Stark water trap attached for 1.5 h. During this time an orange solid deposited, which, on cooling, was filtered off, washed with toluene and dried in vacuo at 125° C. for 3 days to give 80 mg of 6-cyano-3-(3,5-dibromo-4-hydroxy-benzylidene)-1,3-dihydro-indol-2-one; 1H-NMR (DMSO-d6): δ11.05 (bs, 1H), 8.86 (s, 2H), 7.97 (s, 1H), 7.85 (d, J=7.9 Hz, 1 H), 7.50 (d, J=7.9 Hz, 1 H), 7.20 (s, 1H). Mass spectrum (negative ion electrospray): m/z=417 (M−1, 48%), 419 (M−1, 100%), 421 (M−1, 48%).

Workup

  1. temperaturethe reaction refluxed
  2. temperatureDuring this time an orange solid deposited, which, on cooling
  3. filtrationwas filtered off
  4. washwashed with toluene
  5. customdried in vacuo at 125° C. for 3 days

Sources & evidence

ORD record
ord-7ae2962d4ee847b6b6fd2b8bbd4dcd1d
Source dataset
uspto-grants-2001_07
Patent number
US06268391B1

Reaction notes

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