Hydrochloric Acid → HCID 136346820, compound

HRID 1387410Notes

Reaction equation

HRID 1387410 reaction equation
[CH2:1]1[C:5]2=[C:6]3[C:11](=[CH:12][CH:13]=[C:4]2[NH:3][C:2]1=[O:14])[N:10]=[CH:9][CH:8]=[CH:7]3.[Br:15][C:16]1[CH:17]=[C:18]([CH:21]=[C:22]([Br:25])[C:23]=1[OH:24])[CH:19]=O.[ClH:26]>C(O)(=O)C>[ClH:26].[Br:15][C:16]1[CH:17]=[C:18]([CH:21]=[C:22]([Br:25])[C:23]=1[OH:24])[CH:19]=[C:1]1[C:5]2=[C:6]3[C:11](=[CH:12][CH:13]=[C:4]2[NH:3][C:2]1=[O:14])[N:10]=[CH:9][CH:8]=[CH:7]3

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 181003,5-Dibromo-4-HydroxybenzaldehydeHCID 219070851,3-Dihydro-pyrrolo[3,2-f]quinoline-2-one

Product 1

HCID 136346820HCID 136346820, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
115 °C

Procedure

1,3-Dihydro-pyrrolo[3,2-f]quinoline-2-one (552 mg, 3.00 mmol) was combined with 855 mg (3.05 mmol) of 3,5-dibromo-4-hydroxybenzaldehyde (TCl Chemicals) in 6 mL of glacial acetic acid with 1 mL of concentrated hydrochloric acid. The reaction was stirred at 115° C. for 8 hr, cooled and filtered, washing with ethyl acetate, to give 1.32 g of 1-(3,5-Dibromo-4-hydroxy-benzylidene)-1,3-dihydro-pyrrolo[3,2-f]quinolin-2-one hydrochloride as a brown solid which consisted of a 9/1 mixture of Z/E isomers. Mass spectrum (negative ion chemical ionization): m/z=443 (40%), 445 (100%), 447 (40%). 1H NMR (DMSO-d6): δ7.69 (d, J=8.8 Hz, 1H); 7.93 (dd, J=8.7, 4.9 Hz, 1H); 8.24 (d, J=8.8 Hz, 1H); 8.27 (s, 1H); 8.80 (s, 1H); 9.04 (d, J=4.7 Hz, 1H); 9.51 (d, J=8.6 Hz, 1H); 11.3 (s, 1H).

Workup

  1. temperaturecooled
  2. filtrationfiltered
  3. washwashing with ethyl acetate

Sources & evidence

ORD record
ord-368bb3459e4c48feaba2b5d742a9c639
Source dataset
uspto-grants-2001_07
Patent number
US06268391B1

Reaction notes

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