Formic Acid → HCID 53977657, compound

HRID 1763654Notes

Reaction equation

HRID 1763654 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[N:11]([CH:12]=1)[CH2:10][CH2:9][C:8]1[CH:13]=[CH:14][CH:15]=[CH:16][C:7]=1[C:6]2([CH2:18][CH2:19][CH2:20][N:21]([CH3:23])[CH3:22])O)#N.[CH:24]([OH:26])=[O:25].[C:27]([OH:32])(=[O:31])[C:28]([OH:30])=[O:29]>C(O)C>[CH:1]([C:3]1[CH:4]=[C:5]2[N:11]([CH:12]=1)[CH2:10][CH2:9][C:8]1[CH:13]=[CH:14][CH:15]=[CH:16][C:7]=1[C:6]2=[CH:18][CH2:19][CH2:20][N:21]([CH3:23])[CH3:22])=[O:25].[C:27]([OH:32])(=[O:31])[C:28]([OH:30])=[O:29].[CH:24]([C:3]1[CH:4]=[C:5]2[N:11]([CH:12]=1)[CH2:10][CH2:9][C:8]1[CH:13]=[CH:14][CH:15]=[CH:16][C:7]=1[C:6]2=[CH:18][CH2:19][CH2:20][N:21]([CH3:23])[CH3:22])=[O:26]

Participants

6

Reactant 3

HCID 284Formic AcidHCID 971Oxalic AcidHCID 20310599HCID 20310599, compound

Product 2

HCID 53977657HCID 53977657, compoundHCID 73676001HCID 73676001, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Cyano-11-(3-dimethylaminopropyl)-11-hydroxy-6,11-dihydro-5H-pyrrolo[2,1-b][3]benzazepine (.62 g.) and 6.2 g. Ni-Al 1:1 alloy powder (BDH Chemicals Ltd., Pool England) in 50 ml. 75% formic acid is refluxed for 1 hr. The dark red suspension is cooled, filtered to remove the insolubles, washed with formic acid and evaporated to dryness. The yield of this red oil is 3.4 g. (57%) and it slowly crystallizes on cooling. The oxalate salt of 2-formyl-11-(3-dimethylaminopropylidene)-6,11-dihydro-5H-pyrrolo[2,1-b][3]-benzazepine is prepared by dissolving the above product in the minimum volume of ethanol and adding dropwise a saturated ethanolic solution of oxalic acid. The resulting crystals are collected by filtration and dried to give 2-formyl-11-(3-dimethylaminopropylidene)-6,11-dihydro-5H-pyrrolo[2,1-b][3]benzazepine oxalate, m.p. 181° C. (decomp.).

Workup

  1. temperatureThe dark red suspension is cooled
  2. filtrationfiltered
  3. customto remove the insolubles
  4. washwashed with formic acid
  5. customevaporated to dryness
  6. custom(57%) and it slowly crystallizes
  7. temperatureon cooling
  8. filtrationThe resulting crystals are collected by filtration
  9. customdried

Sources & evidence

ORD record
ord-7528d5080d0143ca9383998b20fde4ec
Source dataset
uspto-grants-1978_09
Patent number
US04112112

Reaction notes

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