3-Nitrobenzaldehyde → HCID 20306576, compound

HRID 1764118Notes

Reaction equation

HRID 1764118 reaction equation
[O:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]([NH2:11])[CH2:3][CH2:2]1.[N+:12]([C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH:18]=O)([O-:14])=[O:13]>C(O)C>[N+:12]([C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH:18]=[N:11][CH:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[O:1][CH2:2][CH2:3]1)([O-:14])=[O:13]

Participants

4

Reactant 2

HCID 74493-NitrobenzaldehydeHCID 49619573,4-Dihydro-2H-1-benzopyran-4-amine

Product 1

HCID 20306576HCID 20306576, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

An 80 g, (0.54 mole) portion of 4-chromanamine, and 650 ml of ethanol were placed in a 2-l, 3-necked flask, equipped with a stirrer and reflux condenser fitted with a drying tube. The slurry was treated with 85 g (0.56 mole) portion of m-nitrobenzaldehyde using rapid mechanical stirring. The reaction mixture was refluxed for 5 hrs., cooled 1 hr. and filtered. The yellow crystalline solid was washed with 100 ml of ethanol, ether, and dried, m.p. 117°-118°. Yield: 115 g (76%).

Workup

  1. customequipped with a stirrer
  2. temperaturereflux condenser
  3. customfitted with a drying tube
  4. temperatureThe reaction mixture was refluxed for 5 hrs
  5. temperature, cooled 1 hr
  6. filtrationand filtered
  7. washThe yellow crystalline solid was washed with 100 ml of ethanol, ether
  8. customdried

Sources & evidence

ORD record
ord-af9017eba49b4999841395986d2365b4
Source dataset
uspto-grants-1978_09
Patent number
US04115407

Reaction notes

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