Sulfuric Acid → 2-carboxy-11-(3-dimethylaminopropylidene)-11H-pyrrolo[2,1-b][3]benzazepine

HRID 1763663Notes

Reaction equation

HRID 1763663 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[N:12]([CH:13]=1)[CH:11]=[CH:10][C:9]1[CH:14]=[CH:15][CH:16]=[CH:17][C:8]=1[C:7]2=[CH:18][CH2:19][CH2:20][N:21]([CH3:23])[CH3:22])(=[O:3])N.S(=O)(=O)(O)[OH:25].N([O-])=O.[Na+]>O>[C:1]([C:4]1[CH:5]=[C:6]2[N:12]([CH:13]=1)[CH:11]=[CH:10][C:9]1[CH:14]=[CH:15][CH:16]=[CH:17][C:8]=1[C:7]2=[CH:18][CH2:19][CH2:20][N:21]([CH3:22])[CH3:23])([OH:3])=[O:25]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 23668193Sodium NitriteHCID 706269012-carbamoyl-11-(3-dimethylaminopropylidene)-11H-pyrrolo[2,1-b][3]benzazepine

Product 1

HCID 541911852-carboxy-11-(3-dimethylaminopropylidene)-11H-pyrrolo[2,1-b][3]benzazepine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 2-carbamoyl-11-(3-dimethylaminopropylidene)-11H-pyrrolo[2,1-b][3]benzazepine (0.112 moles) in 300 ml. of 50% sulfuric acid maintained at 50° C. is added slowly 25 g. of sodium nitrite in 75 ml. of water. At the end of the addition, the solid is filtered, washed with water and air-dried to yield 2-carboxy-11-(3-dimethylaminopropylidene)-11H-pyrrolo[2,1-b][3]benzazepine.

Workup

  1. additionis added slowly 25 g
  2. additionAt the end of the addition
  3. filtrationthe solid is filtered
  4. washwashed with water
  5. customair-dried

Sources & evidence

ORD record
ord-eeb4aec01571413b890a75f0bf2ff792
Source dataset
uspto-grants-1978_09
Patent number
US04112112

Reaction notes

Loading…