Ammonia → HCID 20393354, compound

HRID 1863079Notes

Reaction equation

HRID 1863079 reaction equation
[CH2:1]([N:3]([CH2:27][CH3:28])[CH2:4][CH2:5][N:6]([CH3:26])[C:7](=[O:25])[C:8]([C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=1[C:17](=O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=O)[CH3:2].N.C([BH3-])#[N:31].[Na+]>>[ClH:16].[CH2:1]([N:3]([CH2:27][CH3:28])[CH2:4][CH2:5][N:6]([CH3:26])[C:7]([C:8]1[NH:31][C:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:11]2[C:10]=1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12]2)=[O:25])[CH3:2]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 5003444Sodium cyanoborohydrideHCID 20393335HCID 20393335, compound

Product 1

HCID 20393354HCID 20393354, compound

Procedure

In accordance with the procedure described in Example 3, 16.0 g. of o-benzoyl-p-chlorophenylglyoxylic acid [2-(diethylamino)ethyl]methylamide are reacted with 4.1 g. of ammonia and 1.6 g. of sodium cyanoborohydride. The ether extract containing the free base is concentrated to about 300 ml. and treated with ethereal hydrochloric acid. The precipitated hydrochloride is recrystallized from ethanol, and there is obtained 5-chloro-3-phenylisoindole-1-carboxylic acid [2-(diethylamino)ethyl]methylamide hydrochloride in the form of felt-like greenish crystals having a melting point of 208°-210° C. (decomposition).

Workup

  1. extractionThe ether extract
  2. additioncontaining the free base
  3. concentrationis concentrated to about 300 ml
  4. additionand treated with ethereal hydrochloric acid
  5. customThe precipitated hydrochloride is recrystallized from ethanol

Sources & evidence

ORD record
ord-729e83bffcb14033ab91796ea797da8f
Source dataset
uspto-grants-1979_09
Patent number
US04167632

Reaction notes

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