Hydrochloric Acid → HCID 12270299, compound

HRID 1579876Notes

Reaction equation

HRID 1579876 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([C:17]3[CH:22]=[CH:21][C:20]([OH:23])=[C:19]([C:24]([OH:26])=[O:25])[CH:18]=3)[C:10]3[CH2:11][CH2:12][CH2:13][CH2:14][C:15]=3[CH:16]=2)=[CH:4][CH:3]=1.[CH3:27][N:28](C)C=O.[C-]#N.[Na+].Cl>O>[C:24]([C:19]1[CH:18]=[C:17]([N:9]2[C:10]3[CH2:11][CH2:12][CH2:13][CH2:14][C:15]=3[CH:16]=[C:8]2[C:5]2[CH:4]=[CH:3][C:2]([C:27]#[N:28])=[CH:7][CH:6]=2)[CH:22]=[CH:21][C:20]=1[OH:23])([OH:26])=[O:25]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 8929Sodium CyanideHCID 12270294HCID 12270294, compound

Product 1

HCID 12270299HCID 12270299, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 6.18 g. (0.015 mole) of 2-(4-bromophenyl)-1-(3-carboxy-4-hydroxyphenyl)-4,5,6,7-tetrahydroindole, 1.6 g. (0.018 mole) of cuprous cyanide, and 10 ml. of dimethyl formamide was heated under reflux for 6 hours, poured into a solution of 3 g. of sodium cyanide and 10 ml. of water, and after 5 minutes diluted with 46 ml. of water. The solution was acidified to pH 1-2 with hydrochloric acid and the solid which separated was collected. Recrystallization from acetic acid gave 1.21 g. (23%) of crystals, m.p. 242°-244°.

Workup

  1. additionA mixture of 6.18 g
  2. temperatureunder reflux for 6 hours
  3. additionpoured into a solution of 3 g
  4. customthe solid which separated
  5. customwas collected
  6. customRecrystallization from acetic acid
  7. customgave 1.21 g

Sources & evidence

ORD record
ord-9751813664ef41b78abdb9a3c4a3b998
Source dataset
uspto-grants-1976_01
Patent number
US03931407

Reaction notes

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